TW523506B - Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients - Google Patents

Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients Download PDF

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Publication number
TW523506B
TW523506B TW086118583A TW86118583A TW523506B TW 523506 B TW523506 B TW 523506B TW 086118583 A TW086118583 A TW 086118583A TW 86118583 A TW86118583 A TW 86118583A TW 523506 B TW523506 B TW 523506B
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Taiwan
Prior art keywords
benzoic acid
isopropyl
benzenesulfonamido
acid
trifluoromethylphenoxymethyl
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TW086118583A
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Chinese (zh)
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Shuichi Ohuchida
Yuuki Nagao
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Ono Pharmaceutical Co
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/12—Antidiarrhoeals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/06—Antiabortive agents; Labour repressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/21—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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Abstract

The present invention relates to a compound of formula (I) and a salt thereof: (wherein rings A and B represent a carbocyclic or heterocyclic ring; Z1 represents -COR1, -CH=CH-COR1 etc.; Z2 represents a hydrogen atom, an alkyl group etc.; Z3 represents a bond or an alkylene group; Z4 represents SO2, CO; Z5 represents an alkyl group, a phenyl group or heterocyclic ring; R2 represents CONR8, O, S, NZ6, Z7-alkylene, or alkylene group etc.; R3 represents a hydrogen atom, an alkyl group, a halogen, CF3 etc.; R4 represents a hydrogen atom or substituted alkyl group etc.; n and t each represent an integer of 1-4). The compound of formula (I) is capable of binding with PGE2 receptor and thus exhibit antagonistic or agonistic effects. The compound (I) is useful as a drug for inhibiting retraction of uterus, analgesia, inhibiting the motion of digestive tract, inducing sleep, increasing a volume of the bladder, and useful as a drug for restracting uterus, promoting the motion of digestic tract, inhibiting secretion of gastric juice, hypotension and diruesis.

Description

經濟部中央標準局員工消費合作社印製 523506 Α7 Β7 五、發明説明（l ) 琎明持術镅城 本發明係有翮磺鱅胺或脲衍生物。詳言之，係有醐： (1)通式（I)所示之化合物：Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 523506 Α7 Β7 V. Description of the Invention (l) 琎 明 镅 术 镅 城 The present invention is a sulfonamide or a urea derivative. In particular, it is: (1) a compound represented by the general formula (I):

R4 (式中，各符號具有後逑之相同意義）， (2) 其製造方法，及 (3) 含其作為有效成分之筋列腺素E“後文簡稱為 PGE2)之拮抗或激動_。 習知坊術 PGE2已知為花生四烯酸級聯中之代謝產物，其已知具 有子宮收縮、引發疼痛作用、促進消化道蟠動、興奮作用 、膀胱收縮作用，抑制胃酸分泌作用，降血壓等作用。該 等作用中，拮抗作用及激動作用各預期具有Μ下作用。 對PGE2之拮抗作用，因其抑制作用，而各產生抑制子 宮收縮、縝痛、抑制消化道蓮動、誘眠作用及增勝胱容量 之作用。因此，PGE2拮抗劑可作為預防流產、縝痛劑、止 瀉劑、安眠劑及頻尿治療劑。 又，對PGE2之激動作用，因其促進作用，而各具有子 宮收縮、消化道蓮動亢進、抑制胃酸分泌作用、降血歴作 用及利尿作用等。因此PGE2之激動劑可作為堕胎劑、瀉劑 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 393 3 1 ^^衣-- (請先閱讀背面之注意事項再填寫本頁) 、1Τ 523506 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明（4R4 (in the formula, each symbol has the same meaning as the suffix), (2) its manufacturing method, and (3) antagonism or agonism containing selenostat E (hereinafter referred to as PGE2) as its active ingredient. PGE2 is known as a metabolite in the arachidonic acid cascade. It is known to have uterine contraction, cause pain, promote gastrointestinal motility, excitement, bladder contraction, inhibit gastric acid secretion, and lower blood pressure. Among these effects, each of the antagonistic and agonistic effects is expected to have a lowering effect. The antagonistic effect on PGE2, due to its inhibitory effect, each produces inhibition of uterine contraction, pain, inhibition of gastrointestinal lotus movement, sleepiness, and The effect of increasing cystic capacity. Therefore, PGE2 antagonists can be used as anti-abortion agents, diarrhea agents, antidiarrheal agents, sleeping agents and frequent urination treatment agents. Moreover, the agonistic effect on PGE2 has its uterus due to its promoting effect. Contraction, hyperactivity of the digestive tract lotus, inhibition of gastric acid secretion, lowering blood pressure, diuretic effect, etc. Therefore, agonists of PGE2 can be used as abortion agents and laxatives. This paper applies Chinese national standards (CNS ) Α4 specifications (210X 297 mm) 393 3 1 ^^ clothing-(Please read the precautions on the back before filling out this page), 1T 523506 Α7 Β7 Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 4

Me (E) (式中，RE表示苯乙基、苄基、十六烷基、癸基、壬 基、丁基、丙基、乙基及甲基）。 Khia. Geterotsikl. Soediη ( 1 972 ) , ( 1 0 ) , 1 34 1 中 揭以下化合物：Me (E) (wherein RE represents phenethyl, benzyl, hexadecyl, decyl, nonyl, butyl, propyl, ethyl, and methyl). The following compounds are disclosed in Khia. Geterotsikl. Soediη (1 972), (1 0), 1 34 1:

(請先閱讀背面之注意事項再填寫本頁) (Μ) (F-2) (式中，RF為硝基、甲氧基）。 、 KhiB· Geterotsikl· Soedin(1972), (5), 616中掲 示K下化合物： 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 3933 1 523506 A7 B7 五、發明説明（(Please read the precautions on the back before filling this page) (Μ) (F-2) (where RF is nitro and methoxy). KhiB · Geterotsikl · Soedin (1972), (5), 616 Compounds under K: This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 3933 1 523506 A7 B7 V. Description of the invention (

(G-1)(G-1)

(G-2) (請先閱讀背面之注意事項再填寫本頁) uMe(G-2) (Please read the notes on the back before filling this page) uMe

Khiin· Geterotsikl· Soedin( 1 976 ), (5 ), 641 中掲 示以下化合物：Khiin · Geterotsikl · Soedin (1 976), (5), 641 shows the following compounds:

(Η)(Η)

經濟部中央標準局員工消費合作社印製Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

MeMe

Khii Geterotsikl· Soed i n (1971 ) , (7), 1 028 中揭Khii GeterotsiklSoed i n (1971), (7), 1 028

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 3933 1 523506 kl B7 五、發明説明（This paper size applies to China National Standard (CNS) A4 (210X297 mm) 3933 1 523506 kl B7 V. Description of the invention (

(J-2)(J-2)

Kh i m . Geterots i k 1 . Soedin ( 1 970 ) , ( 1 2), 1 597 中 揭示以下化合物： (K-1) 經濟部中央標準局員工消費合作社印製The following compounds are disclosed in Kh i m. Geterots i k 1. Soedin (1 970), (1 2), 1 597: (K-1) Printed by the Consumer Cooperative of the Central Standards Bureau, Ministry of Economic Affairs

C〇〇H (Κ-2) (請先閱讀背面之注意事項再填寫本頁) (式中，RK各為溴或氯）。 通式（A)、 （B)及（C)所示之先行技術之目的與藥理作 用與本發明相同，但相對於本發明之磺釀胺或脲之必要结 構中，不同處在於醚或伸烷基，由該等结構無法容易類推 本發明。 又，通式（D)至U)所示之化合物，僅作為合成研究， 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 6 3933 1 523506 A7 B7 五、發明説明（7 ) 文獻中完全未記載其藥理作用。又，碳酸鍵结位置係在鄰 位，其構造不同。由該等目的及结構均不同之化合物，無 法類推得本發明。 發明椹示 本發明係有闞： 1) 一種通式（I)所示之磺醢胺或脲衍生物及其無毒性 塩：C〇〇H (Κ-2) (Please read the notes on the back before filling this page) (where RK is bromine or chlorine). The purpose and pharmacological action of the prior art represented by the general formulae (A), (B), and (C) are the same as those of the present invention, but differ from the essential structures of the sulfonamides or ureas of the present invention in the ether or the elongation. Alkyl groups cannot be easily analogized by the present invention from such structures. In addition, the compounds represented by the general formulae (D) to U) are only used for synthetic research. The dimensions of this paper are applicable to the Chinese National Standard (CNS) A4 (210X297 mm) 6 3933 1 523506 A7 B7 5. Description of the invention (7) Its pharmacological effects are not documented at all in the literature. Moreover, the carbonic acid bond position is adjacent, and the structure is different. The present invention cannot be deduced by analogy from compounds having different purposes and structures. Presentation of the invention The present invention includes the following: 1) A sulfonamide or urea derivative represented by the general formula (I) and its non-toxicity 塩:

(請先閱讀背面之注意事項再填寫本頁) ⑴ (式中，及(2 各分別為碳瓌，或含有1 或2個氧、磺或氮原子之5-7員雜環， Z 1表示下列之基： -C0R 1、 -C 1 -4伸烷基-C0R 1、 -CH = CH-C0R 1 , 經濟部中央標準局員工消費合作社印袋 -C班 C-COR 1、 -0-C卜3伸焼基-COR 1 (各式中，R1為羥基、Ct-4烷氧基或式HR6R7之基（式 中，R6及R7各分別為氫或Ci-4烷基）； 或表示式-Ci-5伸烷基-0H之基， Z2表示氫，Cl-4烷基，Cl-4烷氧基，硝基，鹵素，三 氟甲基、三氟甲氧基、羥基或式C0R1之基（式中R1同前逑 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 7 3933 1 523506 A7 B7 五、發明説明（8 ) 定義）， Z3表示單鍵或Ci-4伸烷基， Z4表示S〇2或C0 , Z5表示 (1) Ci-8烷基、C2-8烯基、C2-8炔基， (2) 苯基，C3-7環烷基、含1或2個氧、硫或氮原子之 5-7員雜環， (3) 經苯基或C3-7瓌烷基取代之Ci-4烷基、C2-4烯基 或C2 -4炔基， [上述（2)及（3)中含苯基、C3-7環烷基，含1或2儷氧 、硫或氮原子之5〜7員雜環可經Bi個（BI表示1〜5之整數） R5基（其中，各R5分別為氩、烷基、Ci-6烷氧基、(Please read the precautions on the back before filling out this page) ⑴ (where, and (2 each is a carbon 或, or a 5-7 membered heterocyclic ring containing 1 or 2 oxygen, sulphur or nitrogen atoms, Z 1 represents The following bases: -C0R 1, -C 1 -4 alkylene-C0R 1, -CH = CH-C0R 1,, Central Consumers Bureau of the Ministry of Economic Affairs, Consumer Cooperatives Printing Bags -C Class C-COR 1, -0-C Bu 3 fluorenyl-COR 1 (wherein R1 is a hydroxyl group, a Ct-4 alkoxy group or a group of the formula HR6R7 (wherein, R6 and R7 are each a hydrogen or a Ci-4 alkyl group); or an expression -Ci-5 alkyl of alkyl-0H, Z2 represents hydrogen, Cl-4 alkyl, Cl-4 alkoxy, nitro, halogen, trifluoromethyl, trifluoromethoxy, hydroxyl, or a compound of formula C0R1 Based on the formula (where R1 is the same as the previous one, the paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 7 3933 1 523506 A7 B7 5. Description of the invention (8) definition), Z3 means single bond or Ci-4 extension Alkyl, Z4 represents S02 or C0, Z5 represents (1) Ci-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, (2) phenyl, C3-7 cycloalkyl, containing 1 or 5-7 membered heterocycles with 2 oxygen, sulfur or nitrogen atoms, (3) Ci-4 alkyl, C2-4 alkenyl or C2-4 alkynyl, [5 to 7-membered heterocyclic rings containing phenyl, C3-7 cycloalkyl, 1 or 2 oxo, sulfur or nitrogen atoms in (2) and (3) above may be passed through Bi ( BI represents an integer of 1 to 5) R5 group (wherein each R5 is argon, alkyl, Ci-6 alkoxy,

Ci-6烷硫基、硝基、鹵素、三氟甲基、三氟甲氧基或羥基 )所取代], R 2表示下列之基： CONR8> HR8CO, 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) C0HR8-Ci-4伸燒基、 C 1 -4伸烷基-COHR8、 NR8C0-Ci-4 伸烷基、 <Ci-6 alkylthio, nitro, halogen, trifluoromethyl, trifluoromethoxy or hydroxy)), R 2 represents the following bases: CONR8> HR8CO, printed by the Employees' Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs (Please read the notes on the back before filling out this page) C0HR8-Ci-4 alkylene, C 1-4 alkylene-COHR8, NR8C0-Ci-4 alkylene, <

Ci-4伸烷基- NR8CO、Ci-4 alkylene-NR8CO,

Ci-3伸烷基-C0HR8-Ci-3伸烷基、Ci-3 alkylene-C0HR8-Ci-3 alkylene,

Ci-3 伸基- NR8C0-Ct-3伸烷基、 (各式中，R8表示氫或Ci-4烷基）、 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 8 3933 1 523506 kl B7 五、發明説明（11 ) 基，己炔基，庚炔基，辛炔基及其異構體。 通式（I)中，R4中之Ci-4烷氧基，Z2及R1表示之Ci-4 烷氧基，意指甲氧基、乙氧基、丙氧基、丁氧基及其異構 體。 通式（I)中，R3及R5表示之Ci-6烷氧基，意指甲氧基 、乙氧基、丙氧基、丁氧基、戊氧基、己氧基及其異構體 〇 通式（I)中，R3及R5表示之Ci-6烷硫基，意指甲磙基 、乙硫基、丙硫基、丁硫基、戊硫基、己硫基及其異構體 Ο 通式（I)中，Z1及R2中之Ci-3伸烷基，意指亞甲基、 伸乙基、三亞甲基及其異構體。 通式（I)中，Z1及Z2中之C^-4伸烷基、Z3表示之Ci-4 伸烷基，意指亞甲基、伸乙基、三亞甲基、四亞甲基及其 異構體。 通式（I)中，Z1中之Ci-5伸烷基，意指亞甲基、伸乙 基、三亞甲基、四亞甲基、五亞甲基及其異構體。 經濟部中央標準局員工消費合作社印製 通式（I)中，R2表示之C2-4伸烷基，意指伸乙基、三 亞甲基、四亞甲基及其異構體。 通式（I)中，R2表示之C2-4伸烯基，'意指伸乙烯基、 伸丙烯基、伸丁烯基及其異構體。 通式（I)中，R2表示之C2-4伸炔基，意指伸乙炔基、 伸丙炔基、伸丁炔基及其異構體。 通式（I)中，Z5及R4中之C3-7環烷基，Z5及R4表示之 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 39331 (請先閲讀背面之注意事項再填寫本頁) 11 523506 A7 B7 五、發明説明（12 ) C3-7環烷基，意指環丙基、環丁基、環戊基、環己基、環 庚基。 通式（I)中，及0表示之C5-15碳環，意指單 環、二雙、三環之CS-1S碳環芳基，或其部份或全部飽和 之環。 例如，C5-15碳環芳基，例如苯、戊搭烯（pentalene) 、茚、蔡、莫（azuiene)、 ^(fluorene)、藤等。而 C5-15 碳環芳基之部份或全部飽和之環，例如上逑環之部份或全 部飽和之環。 C5-15碳環，較好為單環、二環之Cs-10碳環芳基及前 逑之C5-7環烷基，更好為笨、萘、環戊基、環己基、環庚 基。 通式（I)中， ©、0及Μ示之含 1或2傾氧、 硫或氮原子之5-7員雜環，意指含1或2個氧、硫或氮原子 之5-7員雜環或其部份或全部飽和之環。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 含1或2個氧、硫或氮原子之5-7員雜環芳基，例如吡 咯、眯唑、吡唑、吡啶、吡_、嘧啶、嗒_、吖庚因、二 吖庚因、呋喃、吡喃、庚因、嗒睡庚因、《盼、0；喃、 thiepine、Β等唑、異Β等唑、《唑、異_：唑、a弩二唑、|咢二 姘、垮吖庚因、鸣二吖庚因、《二唑、《：二畊、躔二吖庚 因環等。 又，含1或2個氧、硫或氮原子之5-7員雜環芳基之部 份或全部飽和之環，例如吡咯啉、吡咯烷、咪唑啉、咪唑 烷、吡唑啉、吡唑烷、六氫吡啶、六氫吡畊、四氫嘧啶、 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 丄 Ζ ό U ό ό i 523506 A7 B7 13 五、發明説明（ 四氫嗒畊、二氫呋喃、四氫呋喃、二氫吡喃、四氫吡喃、 二氫《吩、四氫睡吩、二氫睡喃、四氫β喃、二氫噚唑、 四氫鸣唑、二氫異鸣唑、四氫異鸣唑、二氫瘭唑、四氫α 唑、二氫異噬唑、四氫異鼴唑、嗎咐、硫嗎啉環等。 通式（I)中，Ζ2, R3及R5表示之鹵原子，意指氯、溴 、氟、碘。 通式（I)中，Ζ3表示單鍵或前述之C 為單鍵或亞甲基，更好為單鍵。 伸烷基，較好 經濟部中央標準局員工消費合作社印製 通式（I)中，Ζ4可為任何基，但較好為S〇2。 通式（I)中，R4可為任何基，但較好為氩K外之基。 本發明中，若無特別指示則包含異構艚。例如，烷基 、伸烷基及伸烯基包含直鍵及分枝鐽者，伸烯基中之雙鍵 包含E、Z及EZ混合物。又，存在有分枝鐽烷基時則包含存 在有不對稱碳原子所產生之異構體。 通式（I)所示之本發明化合物中，較好之化合物為 表示C5-15碳環，Z5為Cl-8烷基，C2-8烯基 ,C2-8炔基或含苯基或C3-7環烷基之基（各環可具有取代 基）之化合物。更好為(2)及（J)表示單環、二環之 C5-10碳環芳基及C5-7環烷基，Z5如上述之化合物。 又，Μ 及Ζ5中至少一個基為含1或2個氧 (請先閱讀背面之注意事項再填寫本頁) 較 硫或氮原子之5〜7員雜環（各環可具有取代基之化合物 佳；該等化合物為例如（1) (J) 及表示Cs-1S碳 環，Z5為含1或2傾氧、磙或氮原子之5〜7員雜環之化合物 ，或（2) (J)及(Jj中任一者之基為含1或2個氧、硫或^ Twm 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 523506 A7 B7 五、發明説明（14 ) 氮原子之5〜7員雜環，另一基為C5-15碳環之化合物。更 好為（1)、 （2)之例中，及/或2 表示之碳環為單 環、二環之C5-l0碳瓌芳基及C5-7環烷基之化合物。 通式（1)所示之本發明化合物中，具體較好之化合物 舉例如實施例所載之化合物及其對應之酷及醢胺。 [塩] 通式（I)所示之本發明化合物可藉已知方法轉變成對 應之塩。塩較好為無毒性且水溶性者。缠當之塩為鹼金羼 (鉀、納等）之塩，鐮土金羼（鈣、鎂等）之塩，銨塩，蕖學 可接受之有機胺（四甲銨、三乙胺、甲胺、二甲胺、瓖戊 胺、苄胺、苯乙胺、六氫吡啶、單乙酵胺、二乙酵胺、蠢 (羧甲基）甲胺、賴氨酸、精氨酸、N-甲基-D-葡糖胺等）之 塩。 [本發明化合物之製造方法] 通式（I)所示之本發明化合物可藉下逑方法、後逑實 施例所載之方法或公知方法製造而得。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) (1)通式（I)所示本發明化合物之羧酸化合物，亦即通 式（la)所示之化合物：Ci-3 Extender-NR8C0-Ct-3 Extender, (In each formula, R8 represents hydrogen or Ci-4 alkyl), this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 8 3933 1 523506 kl B7 V. Description of the invention (11) group, hexynyl, heptynyl, octynyl and its isomers. In the general formula (I), Ci-4 alkoxy in R4, Ci-4 alkoxy represented by Z2 and R1, meaning nailoxy, ethoxy, propoxy, butoxy and its isomers . In the general formula (I), Ci-6 alkoxy represented by R3 and R5 means nailoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy and its isomers. In the formula (I), Ci-6 alkylthio group represented by R3 and R5, succinyl group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group and isomers thereof. In (I), Ci-3 alkylene in Z1 and R2 means methylene, ethylene, trimethylene and its isomers. In general formula (I), C ^ -4 alkylene in Z1 and Z2, and Ci-4 alkylene represented by Z3 means methylene, ethylene, trimethylene, tetramethylene and the like isomer. In the general formula (I), Ci-5 alkylene in Z1 means methylene, ethylene, trimethylene, tetramethylene, pentamethylene and its isomers. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs In the general formula (I), C2-4 alkylene represented by R2 means ethylene, trimethylene, tetramethylene and its isomers. In the general formula (I), C2-4 alkenyl represented by R2 means' vinyl, propenyl, butenyl and its isomers. In the general formula (I), C2-4 alkynyl represented by R2 means ethynyl, propynyl, butynyl and its isomers. In the general formula (I), the C3-7 cycloalkyl group in Z5 and R4, and the paper size indicated by Z5 and R4 are applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 39331 (Please read the notes on the back first Please fill in this page again for matters) 11 523506 A7 B7 V. Description of the invention (12) C3-7 cycloalkyl means cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl. In the general formula (I), the C5-15 carbocyclic ring represented by 0 means a monocyclic, bibicyclic, tricyclic CS-1S carbocyclic aryl group, or a partially or fully saturated ring thereof. For example, a C5-15 carbocyclic aryl group, such as benzene, pentalene, indene, tsai, azuiene, fluorene, rattan, and the like. The C5-15 carbocyclic aryl group is partially or fully saturated, such as a partially or fully saturated ring of the upper ring. The C5-15 carbocyclic ring is preferably a monocyclic or bicyclic Cs-10 carbocyclic aryl group and a prosthetic C5-7 cycloalkyl group, more preferably benzyl, naphthalene, cyclopentyl, cyclohexyl, cycloheptyl . In general formula (I), 5-7 membered heterocyclic rings containing 1 or 2 oxygen, sulfur or nitrogen atoms represented by ©, 0 and M mean 5-7 members containing 1 or 2 oxygen, sulfur or nitrogen atoms Member heterocyclic ring or a part or all of it saturated ring. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) 5-7 member heterocyclic aryl groups containing 1 or 2 oxygen, sulfur or nitrogen atoms, such as pyrrole, oxazole, Pyrazole, pyridine, pyrimidine, pyrimidine, dahzine, azepine, diazepine, furan, pyran, heptane, daheptene, "zopan, 0; pyran, thiepine, beta, etc. Isoxazole, "azole, iso_: azole, a crossbodiazole, | dioxin, diazepin, ming diazepine," diazole, ": two farming, diazepine ring and so on. Also, a partially or fully saturated ring of a 5-7 member heterocyclic aromatic group containing 1 or 2 oxygen, sulfur or nitrogen atoms, such as pyrroline, pyrrolidine, imidazoline, imidazolidine, pyrazoline, pyrazole Alkane, hexahydropyridine, hexahydropyridine, tetrahydropyrimidine, this paper size applies Chinese National Standard (CNS) A4 (210X297 mm) 丄 Z ό U ό i 523506 A7 B7 13 V. Description of the invention (tetrahydro Dagen, Dihydrofuran, Tetrahydrofuran, Dihydropyran, Tetrahydropyran, Dihydrohydrophene, Tetrahydrophene, Dihydrofuran, Tetrahydroβan, Dihydrooxazole, Tetrahydroazole, Dihydropyran Isoximidine, tetrahydroisoimidazole, dihydrooxazole, tetrahydroαazole, dihydroisopyrazole, tetrahydroisoxazole, manganese, thiomorpholine ring, etc. In the general formula (I), Z2 , The halogen atom represented by R3 and R5 means chlorine, bromine, fluorine, and iodine. In the general formula (I), Z3 represents a single bond or the aforementioned C is a single bond or a methylene group, and more preferably a single bond. In the general formula (I) printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs, Z4 can be any base, but is preferably S02. In general formula (I), R4 can be any base, but Good for A group other than K. In the present invention, isomers are included unless otherwise specified. For example, an alkyl group, an alkylene group, and an alkenyl group include a straight bond and a branched fluorene, and a double bond in the alkenyl group includes E, A mixture of Z and EZ. In the presence of a branched fluorenyl group, an isomer derived from the presence of an asymmetric carbon atom is included. Among the compounds of the present invention represented by the general formula (I), a preferred compound is C5. -15 carbocyclic ring, Z5 is Cl-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group or a compound containing a phenyl group or a C3-7 cycloalkyl group (each ring may have a substituent). Better (2) and (J) represent a monocyclic or bicyclic C5-10 carbocyclic aryl group and a C5-7 cycloalkyl group, and Z5 is a compound as described above. In addition, at least one of M and Z5 contains 1 or 2 Oxygen (please read the precautions on the back before filling out this page) is better than the 5-7 member heterocyclic ring of sulfur or nitrogen atom (each ring may have a substituent compound; these compounds are for example (1) (J) and Represents a Cs-1S carbocyclic ring, Z5 is a 5- to 7-membered heterocyclic compound containing 1 or 2 oxygen, fluorene, or nitrogen atoms, or (2) the base of any of (J) and (Jj is 1 or 2 2 oxygen, sulfur or ^ Twm National Standard (CNS) A4 specification (210X 297 mm) 523506 A7 B7 V. Description of the invention (14) 5- to 7-membered heterocyclic ring of nitrogen atom, the other group is a C5-15 carbocyclic compound. More preferably ( In the examples of 1) and (2), the carbocyclic ring represented by and / or 2 is a monocyclic or bicyclic C5-l0 carboaryl group and a C5-7 cycloalkyl compound. Among the compounds of the present invention, specific and preferable compounds include, for example, the compounds described in the Examples and their corresponding amines and amidines. [塩] The compounds of the present invention represented by the general formula (I) can be converted into corresponding ones by known methods. Alas. Is preferably non-toxic and water-soluble. The entanglements are alkali metal (potassium, sodium, etc.), sickle metal (calcium, magnesium, etc.), ammonium, and scientifically acceptable organic amines (tetramethylammonium, triethylamine, methylamine). Amine, dimethylamine, pentylamine, benzylamine, phenethylamine, hexahydropyridine, monoethylenzyme, diethylenamine, stupid (carboxymethyl) methylamine, lysine, arginine, N- Methyl-D-glucosamine, etc.). [Production method of the compound of the present invention] The compound of the present invention represented by the general formula (I) can be produced by the following method, the method described in the following examples, or a known method. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the notes on the back before filling this page) (1) The carboxylic acid compound of the compound represented by the general formula (I), which is also represented by the general formula (la) Compounds:

(式中，乙^及^&各表示與Z1及Z2相同定義，但其至 少一基表示COOH或含COOH之基，其他符號表示與前述相同 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 14 3 9 33 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（15 之定義）； 係使通式（lb)所示之酿化合物 (R3b)n(In the formula, B ^ and ^ & each represent the same definition as Z1 and Z2, but at least one base thereof represents COOH or a base containing COOH, and other symbols represent the same as the foregoing. The Chinese paper standard (CNS) A4 specification applies to this paper size. (210X 297 mm) 14 3 9 33 1 523506 A7 B7 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (definition of 15); the brewing compound (R3b) n represented by the general formula (lb)

Z 1b (Z2b)t (lb) 2 Z3-N-Z4- 2^bZ 1b (Z2b) t (lb) 2 Z3-N-Z4- 2 ^ b

R 4b (式中，Zlb及Z2b各表示z1及z2所示之相同定義，但 至少一基為CORlb或含CORib之基（各基中，Rib表示Cl-4烷 氧基或甲氧甲氧基（後文略稱為0Μ0Μ基）），R4b及Z5b 各表示R3, R4及Z5之相同定義，若R3, R4或Z5中之R5表示 C00H或羥基，或含C00H或羥基之基時，各C00H、羥基表示 經可藉酸性、中性或鐮性條件下脫離之保護基予Μ保護之 C00H或羥基，其他符號具前述相同定義 在鐮性、酸性或中性條件下水解，及視需要進一步依不同 之條件下水解而製得。 上述之鹸性、酸性、中性條件下水解而脫離保護基為 後逑之已知反應。 (2)通式（I)所示之本發明化合物之酿化合物，亦即通 式（I c )所示之化合物 (R3)nR 4b (wherein Zlb and Z2b each have the same definition as shown in z1 and z2, but at least one group is CORlb or a group containing CORib (in each group, Rib represents Cl-4 alkoxy group or methoxymethoxy group (Hereinafter abbreviated as 0M0M group)), R4b and Z5b each represent the same definition of R3, R4 and Z5, if R5 in R3, R4 or Z5 represents C00H or hydroxyl group, or each group containing C00H or hydroxyl group, each C00H The hydroxyl group means C00H or hydroxyl group protected by M through a protecting group that can be detached under acidic, neutral or sickle conditions. Other symbols have the same definitions as above. They are hydrolyzed under sickle, acidic or neutral conditions, and if necessary, It is prepared by hydrolysis under different conditions. The above-mentioned known reaction in which the alkaline, acidic, and neutral conditions are hydrolyzed and the protective group is released is the subsequent reaction. (2) A brewing compound of the compound of the present invention represented by the general formula (I) , That is, the compound (R3) n represented by the general formula (I c)

z1c 2c\ (Z， (Ic) (請先閱讀背面之注意事項再填寫本頁) 2 Z3-N — Z4 — Z5 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 15 3933 1 523506 ΑΊ Β7 五、發明説明（16 ) (式中，Z1G&Z2G各與Ζ1及Ζ2具相同定義，但至少一 基為C0R1C或含C0Rlc之基（各基中，R1C表示Ci-4烷氧基）， 其他符號具前述相同定義），係使通式（la)所示之化合物 進行簾化反應而製得。 _化反應為已知，例如 (a) 使用重氮烷之方法， (b) 使用鹵化烷之方法， (c) 使用DMF-二烷基乙縮醛之方法， (d) 與對應之烷酵反應之方法。 以下具驩說明該等方法，U)使用重氮烷之方法為例 如，使用對應之重氮烷，在有櫬溶劑（乙醚、乙酸乙_、 二氯甲烷、丙酮、甲醇、乙酵等）中，在-10T：至401C進行 反應。 (b) 使用鹵化烷之方法為例如，在有機溶劑（丙_、 DMF、DMS0等）中，在鹸（碳酸鉀、碳酸納、碳酸氫鉀、碳 酸氫納、氧化鈣等）存在下，使用對應之鹵化烷，在- ίου 至40TC進行反應。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) (c) 使用DMF-二烷基乙縮醛之方法為例如，在有機溶 劑（苯、甲苯等）中，使用對應之DMF-二烷基乙縮醛，在 -101C至401C進行反應。 < (d) 與對應之烷酵反應之方法為例如，於對應之酵（ HR1G(式中與前述具相同定義））中，使用酸（塩酸、磙 酸、對-甲苯磺酸、氯化氫氣顦等，或縮合劑（DCC、三甲 基乙醢鹵化物、芳磺釀鹵化物、烷磺醸鹵化物等），在0〜 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 16 3933 1 523506 A7 B7 五、發明説明（17 ) 40 t：進行反應。 不用說，該等_化反應可添加不影響反應之有機溶劑 (四氫呋喃、二氯甲烷等）予Μ進行。 (3)通式（I)所示之本發明化合物之醢胺化合物，亦即 通式（Id)所示之化合物： R2z1c 2c \ (Z, (Ic) (Please read the notes on the back before filling in this page) 2 Z3-N — Z4 — Z5 This paper size applies to China National Standard (CNS) A4 (210X 297 mm) 15 3933 1 523506 ΑΊ B7 V. Description of the invention (16) (In the formula, Z1G & Z2G each has the same definition as Z1 and Z2, but at least one group is C0R1C or a group containing C0Rlc (in each group, R1C represents Ci-4 alkoxy Group), and other symbols have the same definitions as above, are obtained by subjecting a compound represented by the general formula (la) to a curtain reaction. A chemical reaction is known, for example, (a) a method using a diazane, (b ) A method using a halogenated alkane, (c) A method using DMF-dialkyl acetal, (d) A method for reacting with a corresponding alkanease. The methods are described below, U) A method using a diazoalkane For example, using the corresponding diazoalkane, the reaction is performed in a solvent containing diethyl ether (ethyl ether, ethyl acetate, dichloromethane, acetone, methanol, ethyl acetate, etc.) at -10T: to 401C. (b) The method of using an alkyl halide is, for example, use in an organic solvent (such as propylene, DMF, DMS0, etc.) in the presence of thallium (potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, calcium oxide, etc.) The corresponding halogenated alkane is reacted at -ίου to 40TC. Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) (c) The method of using DMF-dialkylacetal is, for example, in organic solvents (benzene, toluene, etc.) The reaction was performed at -101C to 401C using the corresponding DMF-dialkylacetal. < (d) The method of reacting with the corresponding alkanes is, for example, to use the corresponding enzyme (HR1G (in the formula has the same definition as above)), using an acid (gallic acid, gallic acid, p-toluenesulfonic acid, hydrogen chloride)顦, etc., or condensing agents (DCC, trimethylacetamidine halide, aromatic sulfonate halide, alkanesulfonium halide, etc.), 0 ~ This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) ) 16 3933 1 523506 A7 B7 V. Description of the invention (17) 40 t: The reaction is carried out. Needless to say, the reaction can be performed by adding an organic solvent (tetrahydrofuran, dichloromethane, etc.) which does not affect the reaction. (3 ) The amidine compound of the compound of the present invention represented by the general formula (I), that is, the compound represented by the general formula (Id): R2

(R3)n —（ B /z1d (Z2d)t 2 Z3-N-Z4 — z5 R4 (Id) (請先閱讀背面之注意事項再填寫本頁) (式中，各與z1及z2所示相同定義，但至少 一基表示CORN或含C0Rld之基（各基中，Rid表示式NR6R7( 式中，全部符號具有與前逑相同之定義）），係使通式（la) 所示之化合物與通式（III)所示之化合物： HHR6R7 (III) (式中，全部符號具有與前述相同之定義）進行醢胺化 反應而製得。 經濟部中央標準局員工消費合作社印製 醢胺化反應為已知者，例如，在惰性有機溶劑（THP, 二氯甲烷，笨，丙醑，乙腈等）中，在三級胺（二甲胺吡啶 ，吡啶，三乙胺等）存在或不存在下，使用縮合繭（EDC、 D C C )等）在0〜5 0 t：進行。 (4)通式（I)所示之本發明化合物之酵化合物，亦即通 式（Ie)所示之化合物： 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 17 39331 523506 A7 B7 五、發明説明（18 7 1e(R3) n — (B / z1d (Z2d) t 2 Z3-N-Z4 — z5 R4 (Id) (Please read the precautions on the back before filling this page)) (In the formula, each is the same as z1 and z2 Definition, but at least one base represents CORN or a base containing CORld (in each base, Rid represents the formula NR6R7 (where all symbols have the same definitions as in the previous paragraph)), which means that the compound represented by general formula (la) and A compound represented by the general formula (III): HHR6R7 (III) (where all symbols have the same definitions as above) are prepared by amidation reaction. The amidation reaction is printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs It is known, for example, in an inert organic solvent (THP, dichloromethane, benzyl, propane, acetonitrile, etc.) in the presence or absence of a tertiary amine (dimethylamine pyridine, pyridine, triethylamine, etc.) The use of condensed cocoons (EDC, DCC, etc.) is performed at 0 to 50 t: (4) the leaven compound of the compound of the present invention represented by the general formula (I), that is, the compound represented by the general formula (Ie): This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 17 39331 523506 A7 B7 V. Description of the invention (18 7 1e

(le) R4 (式中表示Ci-5伸烷基-OH,其他符號具前逑相同 定義 >,係使通式（If)所示之化合物：(le) R4 (where Ci-5 is alkyl-OH, the other symbols have the same meaning as before) > are compounds represented by the general formula (If):

(R3)n-( B Z1f (Z2)t (if) (請先閱讀背面之注意事項再填寫本頁) 2 Z3-N-Z4- Z5 R4 (式中，Zlf表示式伸烷基-COOYM式中， 表示Ci-4烷基）之基，其他符虢具前逑相同定義），進行 缠原反應而製得。 經濟部中央標準局員工消費合作社印製 該還原反應為已知者，係在惰性有櫬溶劑（THF,二氯 甲烷，乙醚，低级烷酵等）存在下，使用氫化鋰鋁（LAH)或 氫化二異丁基鋁（DIBAL)在- 78tJ至室溫進行。 (5)通式（lb)中，R2 為 CONR8、Ci-4 伸烷基- C0NR8、 C0HR8-Ci-4伸烷基或Ci-3伸烷基-C0NR8-Ci-3伸烷基（式中 所有符號具前述之相同定義）之基之通式（Ib-1)所示之化 合物： 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 18 3933 1 523506 A7 B7(R3) n- (B Z1f (Z2) t (if) (Please read the precautions on the back before filling in this page) 2 Z3-N-Z4- Z5 R4 (where Zlf represents the formula alkylene-COOYM formula In the above, Ci-4 represents a group of Ci-4 alkyl), and the other symbols have the same definition as before) and are prepared by entanglement reaction. Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. The reduction reaction is known. It uses lithium aluminum hydride (LAH) or hydrogenated hydrogen in the presence of inert solvents (THF, dichloromethane, ether, lower alkanes, etc.). Diisobutylaluminum (DIBAL) is performed at -78tJ to room temperature. (5) In the general formula (lb), R2 is CONR8, Ci-4 alkylene-C0NR8, C0HR8-Ci-4 alkylene, or Ci-3 alkylene-C0NR8-Ci-3 alkylene (where Compounds of general formula (Ib-1) where all symbols have the same definition as above: This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 18 3933 1 523506 A7 B7

Z1b (Z2b)t 5b R ‘ 五、發明説明（19 (lb-1) (式中，R20表示式CONR8, Ci-4伸烷基-C0NR8, - C0NR8-Ci-4伸烷基或Ci-3伸烷基-C0HR8-Ci-3伸烷基（式中 所有符號具前述相同定義）之基，其他符號具前述相同定 義），係使通式（IV)所示之化合物： (請先閱讀背面之注意事項再填寫本頁)Z1b (Z2b) t 5b R 'V. Description of the invention (19 (lb-1) (where R20 represents the formula CONR8, Ci-4 alkylene-C0NR8,-C0NR8-Ci-4 alkylene or Ci-3 Alkyl-C0HR8-Ci-3 Alkyl (all symbols in the formula have the same definitions as above, and other symbols have the same definitions as above) are the compounds represented by general formula (IV): (Please read the back first (Notes for filling in this page)

(R3b)n—B(R3b) n-B

R200-COOH (IV) 2 Z3-N-Z4—Z5bR200-COOH (IV) 2 Z3-N-Z4—Z5b

R 4b (式中，R2GQ表示單鍵或伸烷基，其他符號具前 述相同定義），與通式（V)所示之化合物·· r8hn-r201- 經濟部中央標準局員工消費合作社印製 Z1b (Z2b)t (V) (式中，R2G1表示單鐽或Ci-4伸烷基，其他符號具前 逑之相同定義），進行醸胺化反應而製得。 酿胺化反應Μ前述（3)所載之相同方法進行。 (6)通式（lb)中，R2 為式 NR8C0、Ci-4伸烷基-NR8C0、 HR8C0-Ci-4伸烷基或Ci-3伸烷基-NR8C0-Ci-3伸烷基（式中 ，所有符號具有前述相同定義）之基之通式（Ib-2)所示之 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 19 3933 1 523506 A7 B7 五、發明説明（2 2 ) 〇 (8)通式（lb)中，R2為式NZ6-Ci-4伸烷基、Ci-4伸烷 基- NZ6或Ci-3伸烷基- NZS-Ci-s伸烷基（式中，所有符號具 前述相同定義）所示之基之通式（Ib-4)所示之化合物： 71bR 4b (where R2GQ represents a single bond or an alkylene group, and other symbols have the same definitions as above), and the compound represented by the general formula (V) ... (Z2b) t (V) (In the formula, R2G1 represents monofluorene or Ci-4 alkylene, and other symbols have the same definitions as before.) It is prepared by amidation reaction. The amination reaction M is carried out in the same manner as described in (3) above. (6) In the general formula (lb), R2 is the formula NR8C0, Ci-4 alkylene-NR8C0, HR8C0-Ci-4 alkylene, or Ci-3 alkylene-NR8C0-Ci-3 alkylene (Formula In the above, the paper size indicated by the general formula (Ib-2) with the basis of all symbols having the same definition as above applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 19 3933 1 523506 A7 B7 V. Description of the invention (2 2) 〇 (8) In the general formula (lb), R2 is a formula of NZ6-Ci-4 alkylene, Ci-4 alkylene-NZ6, or Ci-3 alkylene-NZS-Ci-s alkylene A compound represented by the general formula (Ib-4) in which the group (wherein all symbols have the same definitions as described above): 71b

(式中，R23表示式NZe-Ci^伸烷基、Ci-4伸烷基 -NZ6或Ci-3伸烷基- 伸烷基（式中，所有符號具前 逑相同定義）所示之基，其他符號具前述相同定義），係 (a)使通式（VI-la)所示之化合物： ^J^r230-nhz6 (R3b)n (Vl-a) 2 Z3 - N—Z4- Z5b R4b 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) (式中，R23Q表示單鏈或Ci-4伸烷基，其他符號具前 述相同定義），與通式（VII-a)所示之化合物： ^.21b HOC-R231—(Vll-a) (式中，R23i表示單鍵或伸烷基，其他符號具前 本紙張尺度適用中國國家標準（⑽娜（210X 297⑷ 22 3933 1 523506 kl B7 五、發明説明（23 ) 述相同定義），進行适原胺化反應而製得，或 (b)使通式（VI-b)所示之化合物：(In the formula, R23 represents a group represented by the formula NZe-Ci ^ alkylene, Ci-4alkylene-NZ6, or Ci-3alkylene-alkylene (in the formula, all symbols have the same definitions as before), The other symbols have the same definitions as above), (a) the compound represented by the general formula (VI-la): ^ J ^ r230-nhz6 (R3b) n (Vl-a) 2 Z3-N-Z4- Z5b R4b Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) (where R23Q stands for single chain or Ci-4 alkylene, other symbols have the same definitions as above), and the general formula Compounds shown in (VII-a): ^ .21b HOC-R231— (Vll-a) (where R23i represents a single bond or an alkylene group, and other symbols with the previous paper dimensions apply the Chinese national standard (⑽ 娜 ( 210X 297⑷ 22 3933 1 523506 kl B7 V. Description of the invention (23) The same definition as described above) is prepared by performing a suitable amination reaction, or (b) the compound represented by the general formula (VI-b):

(R3b)nH B(R3b) nH B

l^R231-CHO (Vl-b) Z3-N—Z4~Z5bl ^ R231-CHO (Vl-b) Z3-N—Z4 ~ Z5b

R 4b (式中，所有符號具有前逑相同定義），與通式（vil-b )所示之化合物： hz6n-r230- /z1b-1(¾ ^v^(Z2b)t (Vll-b) (請先閱讀背面之注意事項再填寫本頁) (式中，所有符號具有前述相同定義），進行缠原胺化 反應而製得。 上逑U)、 （b>之邐原胺化反應為例如在惰性有機溶_ (甲醇等.）中，在酸性條件下，使用氰硼氫化納等之硼試藥 在0〜5〇υ進行。 (9)通式（lb)中，R2為C2-4伸烯基之通式（Ib-5)所示 經濟部中央標準局員工消費合作社印製 物 合 化 之 R3tR 4b (where all symbols have the same definitions as before), and the compound represented by the general formula (vil-b): hz6n-r230- / z1b-1 (¾ ^ v ^ (Z2b) t (Vll-b) (Please read the notes on the back before filling this page) (In the formula, all symbols have the same definitions as above.) It is prepared by performing the troponization amination reaction. 逑 U), (b > For example, in an inert organic solvent (methanol, etc.), under acidic conditions, a boron reagent such as sodium cyanoborohydride is used at 0 to 50. (9) In the general formula (lb), R2 is C2- 4 The R3t compound printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs is shown by the general formula (Ib-5) of an alkenyl group.

5b 中 式5b Chinese

定 同 相 逑 前 具 號 符 他 其 基 烯 伸 4 嫌 2 C 示 表 5 2 R 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 23 3933 1 523506 A7 B7 五、發明説明（24 義），係使通式（XI)所示之化合物In the same phase, before the sign, it is marked with tachylidene 4 and 2 C shown in table 5 2 R This paper size is applicable to China National Standard (CNS) A4 specification (210X 297 mm) 23 3933 1 523506 A7 B7 V. Description of the invention ( 24 meaning), is a compound represented by the general formula (XI)

(R3b)n—( B(R3b) n— (B

1 R25 Z3-NHR4b z化 (Z2b)t (XI) (式中，所有符號具前逑相同定義），與通式（IX)所示 之化合物：x-z4-z5b (IX) (請先閲讀背面之注意事項再填寫本頁) (式中，所有符號具前逑相同定義），進行磺釀胺化或 醢胺化反應而製得。 磺醸胺化或醢胺化反應係以筋逑（7)所載之相同方法 進行 (10)通式（lb)中，R2為C2-4伸烷基之通式（Ib-6)所示 之化合物： 1cc 經濟部中央標準局員工消費合作社印製 (R3b)n1 R25 Z3-NHR4b zized (Z2b) t (XI) (where all symbols have the same definition as before), and the compound represented by general formula (IX): x-z4-z5b (IX) (please read first Note on the back, please fill in this page again) (In the formula, all symbols have the same definitions as before), it is made by sulfonation amination or amination reaction. The sulfonamidation or amidation reaction is performed in the same manner as in the tendon (7). (10) In the general formula (lb), R2 is a general formula (Ib-6) of C2-4 alkylene. Compound: 1cc (R3b) n printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

^>^(Z2b)t2、z3-n—z4-z5cc I , r4cc (lb-6) (式中，R26表示C2-4伸烷基，Zlcc、Z5ecRR4ee各表 示Zlb、Zst^R4b之相同定義，但各基不表示伸烯基、伸 炔基、含有伸烯基之基及含有伸炔基之基，其他符號具前 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 2 4 3933 1 523506 A7 B7 五、發明説明（25 ) 逑相同定義，係使通式（Ib-5)所示之化合物進行催化邋原 反應而製得。 催化缠原為已知者，例如在氫氣中，於惰性有機溶劑 (THF,烷酵、丙酮等）中，使用邐原觸媒（鈀、鈀-碳、鉑 、氣化鉑等）在0〜50t!進行。 (11)通式（lb)中，R2為C2-4伸烯基之通式（Ib-7)所示 之化合物： (R3b)n^ > ^ (Z2b) t2, z3-n-z4-z5cc I, r4cc (lb-6) (where, R26 represents C2-4 alkylene, Zlcc and Z5ecRR4ee each represent the same definition of Zlb, Zst ^ R4b However, each group does not represent an alkenyl group, an alkenyl group, a base containing an alkenyl group, and a base containing an alkenyl group. Other symbols have the previous paper dimensions and apply the Chinese National Standard (CNS) A4 specification (210X 297 mm). 2 4 3933 1 523506 A7 B7 V. Description of the invention (25) The same definition of 逑 is made by catalyzing the osmogen reaction of a compound represented by the general formula (Ib-5). Catalytic agents are known, for example in In hydrogen, in an inert organic solvent (THF, alkane, acetone, etc.), the use of rhenium catalysts (palladium, palladium-carbon, platinum, platinum vaporized, etc.) is performed at 0 ~ 50t! (11) General formula ( In lb), R2 is a compound represented by the general formula (Ib-7) of C2-4 alkenyl: (R3b) n

1 R27-1 R27-

Z 1b (Z2b)t (lb-7) (請先閱讀背面之注意事項再填寫本頁) 2 Z3 - N—Z4- Z5bZ 1b (Z2b) t (lb-7) (Please read the precautions on the back before filling this page) 2 Z3-N—Z4- Z5b

R 4b (式中，R27表示C2-4伸烯基，其他符號具前述相同定 義），係使通式（XII)所示之化合物：R 4b (wherein R27 represents a C2-4 alkenyl group, and other symbols have the same definitions as described above), which is a compound represented by the general formula (XII):

(R3b)n-{ B 1 .R27-(R3b) n- {B 1 .R27-

Z 1b (Z2b)t 經濟部中央標準局員工消費合作社印製 23—NHR4b (ΧΠ) (式中，所有符號具前逑相同定義），與通式（IX)所示 之化合物： X_Z4-Z5b (IX) (式中，所有符號具前逑相同定義 >,進行磺醢胺化或 釀胺化反應而製得。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 25 39 33 1 523506 A7 B7 五、發明説明（26 ) 磺醢胺化或釀胺化反應係Μ上逑（7)所載之相同方法 進行。 (12)通式（lb)中，R2為式NZ6S〇2(式中所有符號具前 逑相同定義）之通式（Ib-8)所示之化合物： z 1b (R3b)nZ 1b (Z2b) t Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 23—NHR4b (XΠ) (where all symbols have the same definitions as before), and the compound represented by general formula (IX): X_Z4-Z5b ( IX) (In the formula, all symbols have the same definition as above, and are made by sulfonamidation or brewing amination. This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 25 39 33 1 523506 A7 B7 V. Description of the invention (26) The sulfonamide amination or fermentation amination reaction is carried out in the same manner as described in (7). (12) In the general formula (lb), R2 is the formula NZ6S〇2 A compound represented by the general formula (Ib-8) (all symbols in the formula have the same definitions as before): z 1b (R3b) n

Ur28 (Z2b)t (lb-8) 2 Z3 - N—Z4- Z5b R4b (請先閱讀背面之注意事項再填寫本頁) (式中，R28表示式NZ6S〇2(式中，所有符號具前逑相 同定義），其他符號具前述相同定義），係使通式（Ζ-l)所 示之化合物： (R3b)nUr28 (Z2b) t (lb-8) 2 Z3-N—Z4- Z5b R4b (Please read the precautions on the back before filling this page) (where R28 represents the formula NZ6S〇2 (where all symbols are preceded by逑 Same definition), and other symbols have the same definitions as above), which makes the compound represented by the general formula (Z-1): (R3b) n

NHZ" (Z-1) Z3-N-Z4-Z5bNHZ " (Z-1) Z3-N-Z4-Z5b

R 4b 經濟部中央標準局員工消費合作社印製 (式中，所有符號具前述相同定義 >,與通式（Z-2)所 示之化合物： ,z1b *(Z2b)t xo2s (Ζ-2) (式中，所有符號具前述相同定義），進行·磺醢胺化反 應而製得。 本紙張尺度適用中國國家標準（⑽娜（2淑歸f ) 26 3933 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（27 ) 磺釀胺化反應，係Μ前述（7)所載之相同方法進行。 (13)通式（lb)中，R2 為式 CO、CO-Ci-4 伸烷基、Ci-4 伸烷基-CO或Ci-3伸烷基-CO-C1-3伸烷基之通式（Ib-9)所 示之化合物： 7 1b (R3b)nR 4b Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (where all symbols have the same definition as above), and compounds represented by the general formula (Z-2):, z1b * (Z2b) t xo2s (Z-2 ) (Where all symbols have the same definitions as above) and are made by sulfonamidation reaction. This paper size applies the Chinese national standard (⑽ 娜 (2 淑 归 f) 26 3933 1 523506 A7 B7 Central Standard of the Ministry of Economy Printed by the Bureau's Consumer Cooperatives V. Description of the Invention (27) The sulfonation amination reaction is performed in the same manner as described in (7) above. (13) In the general formula (lb), R2 is the formula CO, CO-Ci Compound represented by the general formula (Ib-9): -4 alkylene, Ci-4 alkylene-CO, or Ci-3 alkylene-CO-C1-3 alkylene: 7 1b (R3b) n

(lb-9) R (式中，R29表示式CO、CO-Ci-4伸烷基、Ci-4伸烷基 伸烷基-CO-Ci-3伸烷基，其他符號具前逑相同 定義），係使通式（Ζ-3)所示之化合物： 1 R200.C〇C|(lb-9) R (where, R29 represents the formula CO, CO-Ci-4 alkylene, Ci-4 alkylene alkylene-CO-Ci-3 alkylene, and other symbols have the same definitions as before) , Is the compound represented by the general formula (Z-3): 1 R200.C〇C |

(R3b)n-( B 2 z3-n-z4-z 4b (請先閲讀背面之注意事項再填寫本頁) (Z-3) 5b (式中，所有符號具前逑相同定義），與通式（Z-4)所 示之化合物反應而製得： X—R201 Z1b -YaT (z-4) W^(Z2b)t (式中，所有符號具前逑相同定義）。 該反應係例如在惰性有櫬溶_(THF，二氛甲烷、苯、 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 27 3933 1 523506 A7 B7 五、發明説明（28 ) 丙_、乙購等）中，在鋅、镇化_存在下，在- 78υ〜室溫 進行。 (14)通式（lb)中，R4b為氳以外之基之通式（Ib-ΙΟ)所 示之化合物：(R3b) n- (B 2 z3-n-z4-z 4b (Please read the precautions on the back before filling this page) (Z-3) 5b (where all symbols have the same definitions as before), and the same X-R201 Z1b -YaT (z-4) W ^ (Z2b) t (wherein all symbols have the same definitions as before). The reaction is, for example, in Inert solvents: (THF, dichloromethane, benzene, this paper is in accordance with Chinese National Standards (CNS) A4 specifications (210X 297 mm) 27 3933 1 523506 A7 B7 V. Description of the invention (28) Etc.), in the presence of zinc and ballasting, at -78υ ~ room temperature. (14) In the general formula (lb), the compound represented by the general formula (Ib-10) where R4b is a group other than 氲:

ZZ

(Z2b)t (請先閱讀背面之注意事項再填寫本頁) 1b (lb-10) (式中，R44表示除氫K外之同R4之定義，其他符號具 前述之相同定義），係使通式（Ib-ΙΙ)所示之化合物： 7 1b(Z2b) t (Please read the precautions on the back before filling this page) 1b (lb-10) (where R44 represents the same definition as R4 except hydrogen K, and other symbols have the same definitions as above), so Compound represented by the general formula (Ib-III): 7 1b

(lb-11) Η 經濟部中央標準局員工消費合作社印製 (式中，所有符號具前逑之相同定義），與（a)通式 (Z - 5 )所示之化合物： X-R44 (Z-5) (式中，所有符號具前逑之相同定義），或（b)通式 (Z-6)所示之化合物反應而製得： HO-R44 (Z-6) (式中，所有符號具前逑之相同定義）。 上述反應為已知之N -烷化反應或對應之反應。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 28 3933 1 523506 A7 B7 五、發明説明（29 ) 例如，使用（a)X-R44(式中，所有符號具前述相同定 義）所示之鹵化烷時，係在有機溶劑（丙萌、THF、二氯甲 烷等）中，在_ (碳酸鉀等）存在下，在0〜5〇υ之溫度進行 Ο 又，使用（b)HO-R44(式中，所有符號具有前逑相同之 定義）所示之酵時，係在有機溶劑（丙酮、THF、二氯甲烷 等）中，在三苯膦及二乙基偁氮甲醸胺（DEAD)存在下，在0 〜501C之溫度進行。 (15) R3為羥甲基之化合物係Μ上述方法或後述實施例 所述方法製造。 (16) Ζ4為式S〇2之基、Ζ5為環戊基、環己基（各環可經 (R5)m所取代）或異丙基之化合物係Μ上逑方法或後逑實施 例所述方法製造。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) (17) ZiM外之基為C00H、C00Za(基中，Za表示Ci-4烷 基）或羥基或含C00H、C00ZM基中，所有符號具前逑相同 定義）或羥基之化合物製造時，係視情況將包含Z1及上述 各基K在鹼性、酸性或中性條件下可去保護之保護基保護 使其不進行反應；去保護係在鐮性、酸性或中性條件下進 行，或K組合不同條件進行去保護（例如各進行酸性條件 下之去保護及鐮性條件下之去保護，可先進行任一反應） 0 可在酸性條件下去保護之C00H保護基，可為例如第三 丁基二甲基矽烷基之含矽烷基之基、第三丁基等。 可在鐮性條件下去保護之C00H保護基，可為例如第三 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 29 39331 523506 Α7 Β7 五、發明説明（30 )丁基Μ外之烷基（例如甲基等）等。酸性條件及餘性條件下可去保護之C00H保護基，可為 例如甲氧甲基等。中性條件下可去保護之C00H保護基，可為例如苄基等 喃乙 吡基 氫氧 四乙 如1-例 ， 為基 可之 基基 護烷 保矽 基含 羥之 之等 護基 保烷 去矽 可基 C 下甲等 件二基 條基甲 性丁氧 酸三 甲 第 · 、基 等 基 釀 乙 如 例 為 可 基 護 保 基 羥 之 護 保 去 可 下 件 條 性 〇 鹼基中 醢 之 基 苄 如 例 為 可 基 護 保 基 羥 之 護 保 去 可 下 件 條 性 第 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 三丁基二甲基矽烷基等之含矽烷基之基。 鹼性條件下之去保護為已知者，例如在有櫬溶麵（甲 醇、四氫呋喃、二鸣烷等）中，使用_金羼氫氧化物（氫氧 化納、氫氧化鉀等）、鐮土金羼氩氧化物（氫氧化鈣等）或 碳酸塩（碳酸納、碳酸鉀等）之水溶液或其混合物，在0〜 40t：進行。 酸性條件下之去保護為已知者，例如在溶劑（二氯甲 烷、二呜烷、乙酸乙豳、乙酸、水或其混合溶劑）中，使 用有櫬酸（三氟乙酸等）或無機酸（塩酸、隹溴酸等），在0 〜ΐ2〇υ進行。 中性條件下之去保護為已知者，例如苄基之例中，係 有溶劑（_系（四氫呋喃、二鸣烷、二甲氧乙烷、乙_等） 、醇系（甲酵、乙酵等）、笨系（苯、甲苯等）、画系（丙醒 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 30 3933 1 523506 A7 B7 五、發明説明（3 1 ) 、甲基乙基醒等）、腈条（乙猜等）、釀胺系（二甲基甲釀胺 等）、水、乙酸乙簾、乙酸或兩種以上之混合溶劑）中，在 觸媒（鈀-碳、鈀黑、氫氧化鈀、二氧化鉑、阮尼鐮等）存 在下，在常壓或加壓下於氫氣中或在甲酸銨存在下，在0 〜200 t：之溫度進行。 又，在第三丁基二甲基矽烷基等之含矽烷基之例中， 係在溶劑（醚系（四氫呋喃、二鸣烷、二甲氧乙烷、乙醚等 )、酵系（甲酵、乙酵等）、苯系（苯、甲苯等）、酮系（丙醑 、甲基乙基酮等 >、腈条（乙腈等）、醢胺系（二甲基甲醢胺 等）、水、乙酸乙醱、乙酸或兩種Μ上之混合溶劑）中，在 觸媒（鈀-碳，鈀黑、氫氧化鈀、二氧化鉑、阮尼鎳等）存 在下，在常壓或加壓下於氫氣中或在甲酸銨存在下，在0 〜200 1C之溫度進行。 通式（III)、（V)、（νίΠ、（IX)、（VII-a)、（VII-b) 、（Z-2)、 （Z-4)、 （Z-5)、 （Z-6)所示之化合物係已知者或 易依已知方法或後述實施例所載之方法製得。 通式（IV)、 （VI)、 （VIII)、 （X)、 （XI)、 （XII)及（Z-3 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) )所示之化合物係以次頁後所逑之反應圈式（A)〜（F)製得 〇 各反應圈式中，各符號具前述相同定義，或表示下列 定義。 R2G0:單鍵，Ci-4伸烷基； R202:單鍵，Cl_4伸烷基； R2〇3:單鍵，伸烷基； 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 31 3933 1 523506 kl B7 五、發明説明（32(lb-11) 印 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (where all symbols have the same definitions as before), and a compound represented by (a) general formula (Z-5): X-R44 ( Z-5) (where all symbols have the same definitions as before), or (b) the compound represented by the general formula (Z-6) is reacted to obtain: HO-R44 (Z-6) (where, All symbols have the same definition as before). The above reactions are known N-alkylation reactions or corresponding reactions. This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 28 3933 1 523506 A7 B7 V. Description of the invention (29) For example, using (a) X-R44 (where all symbols have the same definitions as above) In the case of the halogenated alkane as shown in the figure, it is carried out in an organic solvent (such as propylene, THF, dichloromethane, etc.) in the presence of _ (potassium carbonate, etc.) at a temperature of 0 to 5 °, and (b ) HO-R44 (wherein all symbols have the same definitions as before) are in the organic solvent (acetone, THF, dichloromethane, etc.), triphenylphosphine and diethylphosphonium In the presence of sulfonamide (DEAD), it is carried out at a temperature of 0 to 501C. (15) The compound wherein R3 is a methylol group is produced by the above-mentioned method or the method described in the examples described later. (16) Compounds in which Z4 is a group of formula S02, Z5 is cyclopentyl, cyclohexyl (each ring may be substituted by (R5) m) or an isopropyl group are described in the above-mentioned method or the following examples. Method manufacturing. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) (17) The bases outside ZiM are C00H, C00Za (in the base, Za represents Ci-4 alkyl) or hydroxyl or containing In the C00H and C00ZM groups, all the symbols have the same definitions as before) or hydroxyl groups, when manufactured, the protective groups containing Z1 and the above-mentioned groups K which can be deprotected under basic, acidic or neutral conditions are protected as appropriate. It does not react; deprotection is performed under sickle, acidic or neutral conditions, or K is combined with different conditions for deprotection (for example, deprotection under acidic conditions and deprotection under sickle conditions may be performed first. Either reaction) 0 The C00H protecting group that can be protected under acidic conditions may be, for example, a silyl-containing group of a third butyldimethylsilyl group, a third butyl group, or the like. The C00H protecting group that can be protected under sickle conditions can be, for example, the third paper size applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 29 39331 523506 Α7 B7 V. Description of the invention (30) Butyl M Outside alkyl (such as methyl etc.). The C00H protecting group which can be deprotected under acidic and residual conditions may be, for example, methoxymethyl. The C00H protecting group that can be deprotected under neutral conditions can be, for example, thioethylpyridyl hydroxide tetraethyl such as benzyl, and the like. For example, it is a base protecting group, a silicon protecting group, a silicon protecting group, and a hydroxyl protecting group. Alkyl succinyl C, dimethyl, dimethyl, butyric acid, butyric acid, trimethyl, and other bases, such as keto and hydroxy, protect hydroxy, and protect the base. For example, the benzyl benzyl group can be protected by the protective base of the hydroxyl group. The article can be downloaded (please read the precautions on the back before filling this page). Silyl-containing groups such as methylsilyl. Deprotection under alkaline conditions is known. For example, in immersed surfaces (methanol, tetrahydrofuran, dioxane, etc.), use _ gold tin hydroxide (sodium hydroxide, potassium hydroxide, etc.), sickle soil Aqueous solutions of gold argon argon oxide (such as calcium hydroxide) or rhenium carbonate (sodium carbonate, potassium carbonate, etc.) or a mixture thereof are performed at 0 to 40t :. Deprotection under acidic conditions is known. For example, in solvents (dichloromethane, dioxane, ethyl acetate, acetic acid, water, or a mixed solvent thereof), osmic acid (trifluoroacetic acid, etc.) or an inorganic acid is used. (Acetic acid, bromic acid, etc.) is performed at 0 to ΐ2〇υ. Deprotection under neutral conditions is known, for example, in the case of benzyl, there are solvents (_ series (tetrahydrofuran, dioxane, dimethoxyethane, ethyl, etc.), alcohols (formaldehyde, ethyl Fermentation, etc.), stupidity (benzene, toluene, etc.), painting (proprietary paper size applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 30 3933 1 523506 A7 B7 V. Description of the invention (3 1) , Methyl ethyl ether, etc.), nitrile strips (ethylamine, etc.), amines (dimethyl methylamine, etc.), water, ethyl acetate, acetic acid or a mixture of two or more solvents), in the catalyst (Palladium-carbon, palladium black, palladium hydroxide, platinum dioxide, Raney sickle, etc.), under normal pressure or pressure in hydrogen or in the presence of ammonium formate, at a temperature of 0 ~ 200 t: . Further, in the case of a silyl group such as a third butyldimethylsilyl group, the solvent (ether type (tetrahydrofuran, dioxane, dimethoxyethane, ether, etc.), and the yeast system (formaldehyde, Acetobacter, etc.), Benzene (Benzene, Toluene, etc.), Ketones (Propanium, Methyl Ethyl Ketone, etc.), Nitrile Bar (Acetonitrile, etc.), Amines (Dimethylformamide etc.), Water , Acetic acid acetate, acetic acid or two mixed solvents on M) in the presence of catalysts (palladium-carbon, palladium black, palladium hydroxide, platinum dioxide, Raney nickel, etc.), at normal pressure or under pressure Under hydrogen or in the presence of ammonium formate, the temperature is 0 to 200 1C. General formula (III), (V), (νίΠ, (IX), (VII-a), (VII-b), (VII The compounds represented by Z-2), (Z-4), (Z-5), (Z-6) are known or can be easily prepared according to known methods or methods described in the examples described later. IV), (VI), (VIII), (X), (XI), (XII), and (Z-3 printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) The compounds shown in) are listed after the next page. The reaction ring formulas (A) to (F) are obtained. In each reaction ring formula, each symbol has the same definition as above, or represents the following definition: R2G0: single bond, Ci-4 alkylene; R202: single bond, Cl_4 ethylene Alkyl; R2 03: single bond, alkylene; This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 31 3933 1 523506 kl B7 V. Description of the invention (32

2 2 2 2 2 5 R R R R R R ο2 2 2 2 2 5 R R R R R R ο

基·， 烷基 伸烷 C2伸 或C3 C1或 2 , C 鍵、 單 CRadical, alkyl, alkylene, C2 or C3, C1 or 2, C bond, single C

基 ·， 烷基 伸烷 C2伸 或C3 C 或 2 f C 建 0 、 單 CBase, alkyl, butane, C2, C3, C, 2f, C, 0, single C

基 烷 伸 2 C 或 1 C ; 基 基釀 烷乙 T氟 C1三 : : ο 1 應 反 之 要 必 有 況 情 ; 視 素為 鹵弧 : 括 X4之 、 中 X3式 、 圓 X2應 、 反 X1各 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 32 3933 1 523506 ΑΊ Β7 五、發明説明（33 2 zfHR# 藤1) (RjnAB 一Alkanes 2 C or 1 C; Alkanes 2 T Fluoro C1 Tri :: ο 1 Should be the opposite, there must be circumstances; the element is halogen arc: Including X4, medium X3, round X2 should, reverse X1 Each (please read the notes on the back before filling out this page) The paper size printed by the staff consumer cooperative of the Central Bureau of Standards of the Ministry of Economy applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 32 3933 1 523506 ΑΊ Β7 V. Invention Description (33 2 zfHR # Vine 1) (RjnAB a

tRi,COOH 經濟部中央標準局員工消費合作社印製 (<) (ζ·3)tRi, COOH Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (<) (ζ · 3)

2^-2¾ (XIV) 蕺隳薄佘 鼸®Mb ζιζ" zh4b2 ^ -2¾ (XIV) 蕺 隳 薄 佘 M®Mb ζιζ " zh4b

(RjnABI(RjnABI

(RjnAB (請先閱讀背面之注意事項再填寫本頁) -RICOORg ΧΙΖΛΖ3 (IX) 函丼fp>) 1¾。丨 COORS ^/Νω±ΙΝΛΝΪ 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 33 39331 523506 A7 B7 五、發明説明（34 ) (I) n>4b(RjnAB (please read the precautions on the back before filling out this page) -RICOORg ΧΙΑΛ3 (IX) Letter 丼 fp >) 1¾.丨 COORS ^ / Νω ± ΙΝΛΝΪ This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 33 39331 523506 A7 B7 V. Description of the invention (34) (I) n > 4b

R—丨 NH ~ zrNHR^"(XVI)R— 丨 NH ~ zrNHR ^ " (XVI)

(RjAB (請先閱讀背面之注意事項再填寫本頁)(RjAB (Please read the notes on the back before filling this page)

xlN4—N5b (IX) 0 0 (3ΠΛΒ 經濟部中央標準局員工消費合作社印製 5bxlN4-N5b (IX) 0 0 (3ΠΛΒ Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5b

Ri-N〇2 ν7Νω±ΙΝΛΝΪ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 34 3933 1 523506 A7 B7 五、發明説明（35 <3 經濟部中央標準局員工消費合作社印製Ri-N〇2 ν7Νω ± ΙΝΛΝΪ This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 34 3933 1 523506 A7 B7 V. Description of the invention (35 < 3 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

^工 Γοζω 丨 Λ/HFicnl β 雜 frr βc/3- ,ζ lb (請先閲讀背面之注意事項再填寫本頁)^ 工 Γοζω 丨 Λ / HFicnl β Miscellaneous frr βc / 3-, ζ lb (Please read the precautions on the back before filling this page)

Nib3t z。丨 NHJJ^Nib3t z.丨 NHJJ ^

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 35 3933 1 523506 A7 B7 五、發明説明（36 ) 2 ΖΓΝΗ2 (XXVI) z 一,3t 經濟部中央標準局員工消費合作社印製This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) 35 3933 1 523506 A7 B7 V. Description of the invention (36) 2 ZΓΝΗ2 (XXVI) z 1. 3t Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

μ/νγνηρ^(Iμ / νγνηρ ^ (I

(Rg)nAB ,3t 22(Rg) nAB, 3t 22

rsl(a X3i4b iDrsl (a X3i4b iD

J lbJ lb

Njt z 1b (請先閲讀背面之注意事項再填寫本頁)Njt z 1b (Please read the notes on the back before filling this page)

Ma画斗 fn)Ma drawing bucket fn)

N 1b 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 36 3933 1 523506 A7 B7 五、發明説明（37N 1b The size of this paper applies to Chinese National Standard (CNS) A4 (210X 297 mm) 36 3933 1 523506 A7 B7 V. Description of the invention (37

b/ζίρ (XXVII)b / ζίρ (XXVII)

(RjnAB 3t(RjnAB 3t

'xa 丨 R 經濟部中央標準局員工消費合作社印製'xa 丨 R Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

Nlb3t z 3b4bNlb3t z 3b4b

7 1b 3t z 1b (請先閱讀背面之注意事項再填寫本頁) FLEIBhIE, 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 37 523506 A7 五、發明説明（387 1b 3t z 1b (Please read the notes on the back before filling this page) FLEIBhIE, This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) 37 523506 A7 V. Description of the invention (38

丨n〇2 、2bx 1b 8〇工 SOCI2 ^ Z⑴丨n〇2 (XXXII) (請先閱讀背面之注意事項再填寫本頁) 3t丨 n〇2, 2bx 1b 8〇 工 SOCI2 ^ Z⑴ 丨 n〇2 (XXXII) (Please read the precautions on the back before filling this page) 3t

Z lb ΔZ lb Δ

Xa-R 3 口4b 經濟部中央標準局員工消費合作社印製Xa-R 3 port 4b Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

Nib3t 3ΠΛΒ ΤΝωιζο^ (XXXVI) N-,3tNib3t 3ΠΛΒ ΤΝωιζο ^ (XXXVI) N-, 3t

Nib IRilcocI Ph3IP-R^-I{g^ (XXXIV) c/3 ΜΝΓΝ02(xxxm) < 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 38 3933 1 523506 A7 B7 五、發明説明（39 ) 本說明書各反應中之反應產物係K 一般純化手段，例 如常壓或減壓蒸餾、使用矽膠或矽酸鎂之高效液體層析法 、薄層層析法、或管柱曆析法或洗淨、再结晶等方法純化 。純化可在各反應時進行，或在反應结束後進行。 [起始物及試藥] 本發明所用之起始物及試蘗，為本身已知者或可依已 知方法製得。 [本發明化合物之藥理活性] 通式（I)所示之本發明化合物可與PGE2受髑结合，而 顯示拮抗或激動作用，而可作為PGE2拮抗麵或PGE2激動劑 〇 如前所述，對PGE2之拮抗作用，而產生抑制子宮收縮 、鎮痛、抑制消化道蓮動、誘眠作用及增大勝胱容量之作 用。因此，1>0£2拮抗麵可作為預防流產、縝痛劑、止瀉劑 、安眠劑及頻尿治療劑。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 又，如前所逑，對PGE2之激動作用，而各具有子宮收 縮、消化道蓮動亢進、抑制胃酸分泌作用、降血壓作用及 利尿作用等。因此PGE2之激動劑可作為墮胎劑、瀉劑、抗 潰瘍劑、抗胃炎劑、降血壓劑及利尿劑。 例如，Μ實驗室之實驗，由使用類前列腺素受體亞型 表現细胞之受體實驗，確認通式（I)所示之本發明化合物 可與PGE2 (ΕΡ1)受體結合。 (i)使用類前列腺素受體亞型表現细胞之受體结合實 驗依據杉本（Suginoto)等人之方法[J. Biol. Che»· 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 39 3933 1 523506 Α7 Β7 五、發明説明（41 ) [表1] 經濟部中央標準局員工消費合作社印製 實施例編號 解離常數Ki U Η) 2 (k) 0.099 18(30) 0.0016 18(38) 0.016 18(58) 0.0062 18(75) 0.0054 18(94) 0 . 0004 18(102) 0·0002 20(20) 0 . 0099 22(3) 0 * 48 24 0 . 0058 24(9) 0.018 30 0.073 38 0.16 43 0 . 38 44 0.0013 48 0*01 、 (請先閱讀背面之注意事項再填寫本頁) [毒性] 本發明化合物之毒性十分低而可相當安 σ ΡΡ 〇 蕖 0 為 作 地 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 41 3933 1 523506 Α7 Β7 五、發明説明（42 ) [轚藥品應用] 通式（I)所示之本發明化合物可與PGE2受體結合，而 顯示拮抗或激動作用，而可作為PGE2拮抗劑或PGE2激動劑 〇 如前所逑，對PGE2之拮抗作用，而產生抑制子宮收縮 、鎮痛、抑制消化道運動、誘眠作用及增大膀胱容量之作 用。因此，？0〖2拮抗劑可作為預防流產、鎮痛劑、止瀉劑 、安眠劑及頻尿治療劑。 又，如前所述，對PGE2之激動作用，而各具有子宮收 縮、消化道運動亢進、抑制胃酸分泌作用、降血壓作用及 利尿作用等。因此PGE2之激動劑可作為墮胎劑、瀉劑、抗 潰瘍劑、抗胃炎劑、降血壓劑及利尿劑。 本發明化合物對PGE2受體，尤其是EPi受體之结合性 強，而預期具有作為縝痛劑、頻尿治療劑之用途。 通式（I)所示之本發明化合物，其無毒性塩或其水合 物，基於上逑目的使用時，通常係Μ全身性或局部Μ經口 或非經口形式投藥。 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 投藥量視年龄、體重、症狀、治療效果、投藥方法、 治療時間等而異，但通常對每一成人W每次lag至lOOmg 範圍内一日一次至數次經口投蕖，或對每一成人每次Μ 0.1m g至l〇Bg範圍内一日一次至數次非經口投藥（較好Μ 靜脈內投藥），或Μ —日1小時至2 4小時範圍內Κ靜脈內持 績投藥。 當然前述中，因投藥量係依種種條件而異，因此亦可 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 42 3 93 3 1 523506 Α7 Β7 五、發明説明（b ) 投與比上述投藥量少之量即已足夠或若必要亦可投與超過 上述範圍之量。 本發明化合物投藥之際，經口投藥可使用固體組成物 、液體組成物及其他組成物，非經口投藥則可使用注射劑 、外用劑、栓劑等。 經口投蕖之固體組成物包含錠劑、丸劑、膠囊劑、粉 劑、顆粒劑等。 膠囊劑中包含硬膠囊及軟膠囊。 該固體組成物中，一或一種以上之活性物質與至少一 種惰性稀釋劑混合，例如乳糖、甘露糖酵、葡萄糖、羥丙 基嫌維素、微晶纖維素、澱粉、聚乙烯吡咯烷酮、矽酸銘 酸鎂。依據一般方法，組成物可含有惰性稀釋劑以外之添 加劑，例如硬腊酸鎂之潤滑劑、纖維素乙酵酸鈣之崩解劑 、穀氨酸或天冬氨酸之溶解肋劑。錠劑或丸劑若霈要可以 白糖、明膠、羥丙基缬維素、羥丙基纖維素酞酸酯等之胃 溶性或腸溶性物質之膜被覆，亦可被覆2層Μ上之被膜。 再者像明膠這種易吸收物質之膠囊亦包含在内。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 經口投蕖之液體組成物包含轚蕖容許之乳劑、溶液劑 、糖漿、甘酏劑等。該等液體組成物中含有一或一種Κ上 之活性物質、一般使用之惰性稀釋劑（例如純水、乙醇）。 該組成物除了惰性稀釋劑Κ外，亦可含有溼潤劑、懸浮劑 之肋劑、甘味劑、矯味劑、芳香劑、防腐劑。 經口投蕖之其他組成物為含有一或一種Μ上之活性物 質，包含依據本發明已知方法處方之噴霧劑。該等組成物 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） 43 3933 1 523506 A7 B7 五、發明説明（44 ) 除惰性稀釋劑M,可含有亞硫酸氫納之安定劑及賦與等張 性之安定化劑，氯化鈉，檸檬酸納之擰檬酸之等張劑。噴 霧劑之製造方法詳載於美國專利第2,868,691號及美國專 利第3,095,355號說明書中。 本發明中非經口投藥之注射劑包含無菌之水性或非水 性溶液劑、懸浮劑、乳劑、水性溶液劑、懸濁劑包含例如 注射用蒸餾水及生理食塩水。非水性溶液劑、懸浮劑包含 例如丙二酵、聚乙二醇、橄欖油等植物油，乙酵等之酵類 、聚山梨糖酵_80(登錄商檷）等。該等組成物又可含有防 腐劑、溼潤劑、乳化劑、分散劑、安定化劑、溶解助劑（ 例如穀氨酸、天冬氨酸）等之補助劑。其可藉通過保留细 菌之濾膜、配合殺菌劑及予以照射而殺菌。又可製造成無 菌之固體組成物，而在使用前Μ殺菌或無菌之注射用蒸餾 水或其他溶劑溶解使用。 非經口投藥之其他組成物含有一種或一種以上之活性 物質，該組成物包含Μ —般方法處方之外用液劑、軟膏、 塗佈劑、直腸內投藥之栓劑及陰道內投藥之子宮托。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) [參考例及實施例] 以下，藉由參考例及實施例詳细說明本發明，惟不因 此限制本發明。 ' 層析分離處所示括弧内之溶劑係表示所用之溶出溶劑 或展開溶劑，其比例係Μ體積比表示。若無特別說明，則 NMR係在氘氯仿溶液中测定。 參者例1 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） 44 3 93 3 1 523506 A7 B7 五、發明説明（46 ) 7 · 6 0 _ 7 · 3 7 ( 4 H , m )， 3 · 8 8 ( 3 H , s ) 參者例3 (請先閱讀背面之注意事項再填寫本頁) 2-苯磺釀胺基-5-氯苯甲酸Nib IRilcocI Ph3IP-R ^ -I {g ^ (XXXIV) c / 3 ΜΝΓΝ02 (xxxm) < This paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) 38 3933 1 523506 A7 B7 V. Invention Explanation (39) The reaction product in each reaction of this specification is K. General purification means, such as atmospheric or reduced pressure distillation, high performance liquid chromatography using silica gel or magnesium silicate, thin layer chromatography, or column analysis Purification by washing or recrystallization. Purification can be performed at each reaction, or after the reaction is completed. [Starters and reagents] The initiators and reagents used in the present invention are known per se or can be prepared according to known methods. [Pharmacological activity of the compound of the present invention] The compound of the present invention represented by the general formula (I) can bind to PGE2 and show an antagonistic or agonistic effect, and can be used as a PGE2 antagonistic surface or a PGE2 agonist. The antagonism of PGE2 has the effect of inhibiting uterine contraction, analgesia, inhibiting digestive tract movement, somnolence, and increasing cysteine capacity. Therefore, 1 > 0 £ 2 antagonistic noodles can be used as anti-abortion agents, pain killers, antidiarrheal agents, sleeping pills and frequent urination treatment agents. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page). Also, as previously explained, it has an agonizing effect on PGE2, and each has uterine contraction, gastrointestinal hyperactivity, and gastric acid inhibition Secretory effect, hypotensive effect and diuretic effect. Therefore, PGE2 agonists can be used as abortion agents, laxatives, anti-ulcer agents, anti-gastritis agents, blood pressure lowering agents and diuretics. For example, experiments in the M laboratory confirmed that the compound of the present invention represented by the general formula (I) can bind to the PGE2 (EP1) receptor by a receptor experiment using a prostaglandin receptor subtype-expressing cell. (i) Receptor binding experiments using prostaglandin receptor subtype-expressing cells were performed according to the method of Suginoto et al. [J. Biol. Che »· This paper is in accordance with Chinese National Standard (CNS) A4 (210X 297) (Mm) 39 3933 1 523506 Α7 Β7 V. Description of the invention (41) [Table 1] Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Example number Dissociation constant Ki U Η) 2 (k) 0.099 18 (30) 0.0016 18 (38) 0.016 18 (58) 0.0062 18 (75) 0.0054 18 (94) 0. 0004 18 (102) 0 · 0002 20 (20) 0. 0099 22 (3) 0 * 48 24 0. 0058 24 (9) 0.018 30 0.073 38 0.16 43 0. 38 44 0.0013 48 0 * 01 、 (Please read the precautions on the back before filling out this page) [Toxicity] The toxicity of the compound of the present invention is very low and can be quite safe σ PP 〇 蕖 0 is used as The size of the paper on the ground applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 41 3933 1 523506 A7 B7 V. Description of the invention (42) [Small drug application] The compound of the present invention represented by the general formula (I) can be used with The PGE2 receptor binds and shows an antagonistic or agonistic effect, and can be used as a PGE2 antagonist or a PGE2 agonist. As previously explained, the antagonism of PGE2 has the effects of inhibiting uterine contraction, analgesia, inhibiting gastrointestinal movement, sleeping effect and increasing bladder capacity. therefore,? 0〗 2 antagonists can be used as anti-abortion, analgesics, antidiarrheal agents, sleeping agents and frequent urination treatment agents. In addition, as described above, each of them has an agonistic effect on PGE2, and each has uterine contraction, hyperactive gastrointestinal movement, inhibition of gastric acid secretion, blood pressure lowering effect, and diuretic effect. Therefore, PGE2 agonists can be used as abortion agents, laxatives, anti-ulcer agents, anti-gastritis agents, blood pressure lowering agents and diuretics. The compounds of the present invention have strong binding properties to PGE2 receptors, especially EPi receptors, and are expected to have utility as a pain killer and a frequent urination therapeutic agent. The compound of the present invention represented by the general formula (I), which is non-toxic, or a hydrate thereof, is usually administered systemically or topically as an oral or parenteral form when it is used for the purpose of hydration. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling out this page). The dosage varies depending on age, weight, symptoms, treatment effect, method of administration, treatment time, etc., but it is usually for each adult W once or several times a day within the range of lag to 100 mg each time, or parenterally once or several times a day within the range of 0.1 mg to 10 Bg per adult per administration (preferably M intravenous (Intravenous administration), or intravenous injection of K in the range of 1 to 24 hours per day. Of course, because the dosage varies according to various conditions, the Chinese paper standard (CNS) A4 (210X 297 mm) can be applied to this paper size 42 3 93 3 1 523506 Α7 B7 V. Description of the invention (b) It is sufficient to administer an amount smaller than the above-mentioned amount or, if necessary, an amount exceeding the above-mentioned range. When the compound of the present invention is administered, solid compositions, liquid compositions, and other compositions can be used for oral administration, and injections, external preparations, suppositories, and the like can be used for parenteral administration. The solid composition for oral administration includes lozenges, pills, capsules, powders, granules and the like. Capsules include hard capsules and soft capsules. In the solid composition, one or more active substances are mixed with at least one inert diluent, such as lactose, mannanase, glucose, hydroxypropylanvitamin, microcrystalline cellulose, starch, polyvinylpyrrolidone, and silicic acid. Ming magnesium acid. According to the general method, the composition may contain additives other than an inert diluent, such as a lubricant of magnesium stearate, a disintegrant of calcium cellulose acetate, a dissolving rib of glutamic acid or aspartic acid. Tablets or pills can be coated with a film of gastric or enteric substances such as white sugar, gelatin, hydroxypropylvalvein, hydroxypropyl cellulose phthalate, etc., or they can also be coated on two layers of film. Furthermore, capsules of easily absorbable substances like gelatin are also included. Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) The liquid composition for oral administration contains permissible emulsions, solutions, syrups, sweeteners, etc. These liquid compositions contain one or one of the active substances on K, and generally used inert diluents (such as pure water, ethanol). In addition to the inert diluent K, the composition may contain a wetting agent, a suspending agent, a rib agent, a sweetener, a flavoring agent, a fragrance, and a preservative. Other compositions for oral administration are those containing one or more active substances, including sprays formulated according to methods known in the present invention. The paper size of these compositions applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 43 3933 1 523506 A7 B7 V. Description of the invention (44) In addition to the inert diluent M, it can contain stabilizers such as sodium bisulfite and Isotonic stabilizer, sodium chloride, sodium citrate isotonic agent. The manufacturing method of the aerosol is described in detail in U.S. Patent No. 2,868,691 and U.S. Patent No. 3,095,355. Injections for parenteral administration in the present invention include sterile aqueous or non-aqueous solutions, suspensions, emulsions, aqueous solutions, and suspensions including, for example, distilled water for injection and physiological food water. Non-aqueous solutions and suspensions include vegetable oils such as malonase, polyethylene glycol, olive oil, etc., yeasts such as acetic acid, polysorbate_80 (registered commercial company), and the like. These compositions may also contain preservatives, wetting agents, emulsifiers, dispersants, stabilizers, dissolution aids (such as glutamic acid, aspartic acid), and other supplements. It can be sterilized by retaining the filter membrane of bacteria, adding a bactericide and irradiating it. It can also be made into a sterilized solid composition, which can be sterilized or sterile distilled water for injection or other solvents before use. Other compositions for parenteral administration contain one or more active substances, and the composition includes liquids, ointments, coatings, intrarectal suppositories, and intrauterine pessaries for external use. Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) [Reference Examples and Examples] Hereinafter, the present invention will be described in detail by reference examples and examples, but it does not limit this invention. '' Solvents in parentheses at the chromatographic separations indicate the dissolution or development solvents used, and their ratios are expressed as M volume ratios. Unless otherwise specified, NMR is measured in a deuterochloroform solution. Participant Example 1 This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 44 3 93 3 1 523506 A7 B7 V. Description of the invention (46) 7 · 6 0 _ 7 · 3 7 (4 H, m ), 3 · 8 8 (3 H, s) Participant Example 3 (Please read the precautions on the back before filling this page) 2-benzenesulfonylamino-5-chlorobenzoic acid

2-苯磺醯胺基-5-氯苯甲酸甲酯（600®g,由參考例2合 成）之THF-甲酵混合溶液（6al+3al)於室溫下，添加2N氯氧 化鈉水溶液（2ffil),攪拌2天。反應混合物中添1N塩酸（4.5 ®1>, K乙酸乙酷萃取，有機曆予Μ洗淨、乾燥，得具下 列物理性質之標題化合物（575ing)。 NMR： δ 10.31(lH,s), 7-99(lH,d), 7 . 92 - 7 · 83 ( 2 Η , m), 7.70(lH，d), 7.63-7.42(4H,m), 6.20(lH,brs) 奮）fe例1 4-(2-苯磺釀胺棊-5-氯苯甲釀胺基）笨甲酸甲酷2-benzenesulfonamido-5-chlorobenzoic acid methyl ester (600®g, synthesized from Reference Example 2) in a THF-formaldehyde mixed solution (6al + 3al) was added at room temperature with a 2N sodium oxychloride aqueous solution ( 2ffil), stir for 2 days. The reaction mixture was added with 1N acetic acid (4.5 ® 1), extracted with ethyl acetate, and washed organically and dried to obtain the title compound (575ing) having the following physical properties. NMR: δ 10.31 (lH, s), 7 -99 (lH, d), 7.92-7 · 83 (2 Η, m), 7.70 (lH, d), 7.63-7.42 (4H, m), 6.20 (lH, brs) Fen) Example 1 4 -(2-benzenesulfonylamine hydrazone-5-chlorobenzylamine)

經濟部中央標準局員工消費合作社印製 及對-胺基苯甲酸甲«(133Bg>之二氯甲烷懸浮液（5ml)中， 添加EDC(168mg)及二甲胺基吡啶（20mg),於室溫下搅拌3 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 46 3933 1 523506 A7 B7 五、發明説明（4 7 ) 天。反應混合物中注入稀塩酸，Μ乙酸乙酷萃取。有機層 予Μ洙淨、乾煉並減壓濃縮。殘留物Μ矽髎管柱層析法（ 乙酸乙釀-苯）純化，得具有下列物理數據之檷題化合物（ 1 4 2 m g ) 〇 TLdRf 0·29(乙酸乙釀：苯=1:9); NHR (CDC 1 3 + DHSO-de) ： δ 10.40(lH,s), 9·90(1Η,πι), 8·03(2Η,(〇, 7·82-7·70(5Η,·), 7.63(lH,d), 7·50-7·24 (4Η，m) , 3·93 (3Η,s) 啻淪锎2 4-(2-苯磺醢胺基-5-氯苯甲醣胺基）苯甲酸 (請先閲讀背面之注意事項再填寫本頁)Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs and p-aminobenzoic acid «(133Bg >) in dichloromethane suspension (5ml), adding EDC (168mg) and dimethylaminopyridine (20mg), in the room Stir at warm temperature 3 This paper is in accordance with Chinese National Standard (CNS) A4 specification (210X 297 mm) 46 3933 1 523506 A7 B7 V. Description of the invention (4 7) days. Dilute acetic acid in the reaction mixture and extract with acetic acid acetic acid. The organic layer was purified, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-benzene) to obtain the title compound (142 mg) with the following physical data. TLdRf 0 · 29 (ethyl acetate: benzene = 1: 9); NHR (CDC 1 3 + DHSO-de): δ 10.40 (lH, s), 9.90 (1Η, π), 8.03 (2Η, (〇, 7.82-7 · 70 (5Η, ·), 7.63 (lH, d), 7.50-7 · 24 (4Η, m), 3.93 (3Η, s) (2-benzenesulfonylamino-5-chlorobenzylamino) benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 4-(2 -苯磺醢胺基-5-氯苯甲醣胺基）苯甲酸甲酿（ 122mg;由實施例1合成）之THF-甲酵溶液（4al+2ml)在室溫 下，加入2H氫氧化納水溶液（0.5·1),攪拌隔夜。反應混 合物中加入2Ν塩酸（0·6Β1)及水，Μ乙酸萃取。有櫬 層予Κ洗淨、乾燥並減壓濃縮。殘留物Μ乙酸乙己烷 再結晶而純化，得具下列物理數據之標題化合物（80ng)。 TLC: Rf 0.32(甲酵：二氯甲烷=15:85); HHR (DHSO-de) ： δ 1 2 . 74 (1 Η , brs) , 10.61(lH,s), 10.40( 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 47 3933 1 523506 A7 B7 五、發明説明h ) lH,s), 7.95(2H,d)， 7·85-7·71(5Η，β〇, 7·64-7·35(5Η, m ) 奮牖例 2(a)-2 (bb) 依參考例1至參考例3及實施例1及2之相同操作，得到 具眘；F列物理數據之標題化合物。 奮_例2 (a) 3-(2-苯磺釀胺基苯甲醸胺基）苯甲酸 〇 (請先閲讀背面之注意事項再填寫本頁)Printed 4- (2-Benzenesulfonylamino-5-chlorobenzylamino) benzoic acid methyl alcohol (122mg; synthesized from Example 1) in THF-formase solution ( 4al + 2ml) At room temperature, a 2H aqueous sodium hydroxide solution (0.5 · 1) was added and stirred overnight. The reaction mixture was added with 2N acetic acid (0.6B1) and water, and extracted with acetic acid. The organic layer was washed with K, dried, and concentrated under reduced pressure. The residue M was purified by recrystallization from ethyl hexane acetate to obtain the title compound (80 ng) having the following physical data. TLC: Rf 0.32 (formaldehyde: methylene chloride = 15: 85); HHR (DHSO-de): δ 1 2. 74 (1 Η, brs), 10.61 (lH, s), 10.40 (This paper is for China National Standard (CNS) A4 specification (210X 297 mm) 47 3933 1 523506 A7 B7 V. Description of the invention h) lH, s), 7.95 (2H, d), 7.85-7 · 71 (5Η, β〇, 7.64-7 · 35 (5Η, m) Fendi Example 2 (a) -2 (bb) Follow the same operation as Reference Example 1 to Reference Example 3 and Examples 1 and 2 to obtain caution; column F physical data The title compound. Fen_ Example 2 (a) 3- (2-benzenesulfonylaminobenzylamino) benzoic acid 0 (Please read the precautions on the back before filling this page)

C〇〇H NH S〇2 丁 L C : R f 0.57 (氯仿··甲酵：乙酸=1 〇 〇 : 1 〇 : 1); NMR (DMSO-dt,) ： ί 13.01 (1H,brs), 10.66 (1H,brs), 10.50 (1H,brs), 8.32 (1H, brs)，7_89 (1H, d)，7.76 (4H, m), 7.51 (6H，m), 7·23 (1H，m)。 經濟部中央標準局員工消費合作社印m 管_例2 (b) 3-(2-苯磺醢胺基-5-氯苯甲醣胺基）苯甲酸C〇H NH S〇2 Butane LC: R f 0.57 (chloroform · formaldehyde: acetic acid = 1 00: 1 0: 1); NMR (DMSO-dt,): 13.01 (1H, brs), 10.66 (1H, brs), 10.50 (1H, brs), 8.32 (1H, brs), 7_89 (1H, d), 7.76 (4H, m), 7.51 (6H, m), 7.23 (1H, m). Printed tube of the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs_Example 2 (b) 3- (2-benzenesulfonamido-5-chlorobenzylamino) benzoic acid

〇 r^| .〇 r ^ |.

Cl\ A八丨Λ^Λ〇〇〇η 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） 48 3933 1 523506 A7 B7 五、發明説明（49 ) TLC : R f 0.26 (氯仿··甲醇=17:3); NMR (CDCI3/DMSO-d6=1:l) ： 12.70 (1H, brs), 10.69 (1H, s), 10.44 (1 Η, s), 8.27 (1H, t), 7.95-7.69 (5H, m), 7.59-7.36 (6H, m)〇 n m m 7(r) 4 -u-苯磺釀胺基笨甲醢胺基）苯甲酸Cl \ A 八 丨 Λ ^ Λ〇〇〇η This paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) 48 3933 1 523506 A7 B7 V. Description of the invention (49) TLC: R f 0.26 (chloroform · · Methanol = 17: 3); NMR (CDCI3 / DMSO-d6 = 1: l): 12.70 (1H, brs), 10.69 (1H, s), 10.44 (1 Η, s), 8.27 (1H, t), 7.95-7.69 (5H, m), 7.59-7.36 (6H, m) 〇nmm 7 (r) 4-u-benzenesulfonylaminobenzylamine) benzoic acid

(請先閲讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

C〇〇H T L C : R f 0·50 (氯仿：甲醇：乙酸=1 〇 〇 : 1 〇 : 1); NMR (DMSO-dfr) ： ^ 12.76 (1H, brs), 10.57 (1H, s), 10.49 (1H, s), 7.95 (2H, d), 7.77 (5H, m), 7.28-7.62 (5H, m), 7.24 (1H, m)〇 管嬾例2 (d) 4-[2-(4-氯苯基）磺釀胺基-5-氯苯甲醢胺基]苯甲酸CO〇HTLC: R f 0.50 (chloroform: methanol: acetic acid = 1 00: 10: 1); NMR (DMSO-dfr): ^ 12.76 (1H, brs), 10.57 (1H, s), 10.49 (1H, s), 7.95 (2H, d), 7.77 (5H, m), 7.28-7.62 (5H, m), 7.24 (1H, m). Example 2 (d) 4- (2- (4 -Chlorophenyl) sulfoamino-5-chlorobenzylamino] benzoic acid

C〇〇H 經濟部中央標率局員工消費合作社印製COOH Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

T L C : R f 0.27 (氯仿：甲醇=1 7 : 3 ); NMR(DMSO-d6)： 5 12.70 (1H, brs), 10.59 (1H, s), 10.30 (1H, s), 7.95 (2H, d)，7.83-7.66 (5H, m), 7.62-7.47 (3H，m), 7_34 (1H, d)。 mm2 (e) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 49 3933 1 523506 A7 B7 五、發明説明（50 ) 4_[2-U-氯苯磺釀胺基卜4-氯苯甲釀胺基]苯甲酸TLC: R f 0.27 (chloroform: methanol = 1 7: 3); NMR (DMSO-d6): 5 12.70 (1H, brs), 10.59 (1H, s), 10.30 (1H, s), 7.95 (2H, d ), 7.83-7.66 (5H, m), 7.62-7.47 (3H, m), 7_34 (1H, d). mm2 (e) This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 49 3933 1 523506 A7 B7 V. Description of the invention (50) 4_ [2-U-Chlorobenzenesulfonylamine 4- Chlorobenzylamino] benzoic acid

XXXX

COOH 'NH S〇2COOH 'NH S〇2

ClCl

丁 L C : R f 0.69 (氯仿：甲醇：乙酸=17:2:1); NMR (CDCI^+DMSO-d6) ： Θ 10.9-10.3 (1H, br), 10.3-9.9 (1H, br)，7.84 (2H， d)，7.7-7.5 (5H，m), 7.45 (1H,似s )，7·17 (2H，d)，7.0-6.9 (1H，m)。 gLte m ?.(f) 4-[2M4-氯笨磺釀胺基）-6-氯苯甲醢胺基]苯甲酸 COOHDLC: R f 0.69 (chloroform: methanol: acetic acid = 17: 2: 1); NMR (CDCI ^ + DMSO-d6): Θ 10.9-10.3 (1H, br), 10.3-9.9 (1H, br), 7.84 (2H, d), 7.7-7.5 (5H, m), 7.45 (1H, like s), 7.17 (2H, d), 7.0-6.9 (1H, m). gLte m?. (f) 4- [2M4-chlorobenzylamine] -6-chlorobenzylamine] benzoic acid COOH

(請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 T L C : R f 0.67 (氯仿：甲醇：乙酸=1 7 : 2 ·· 1 ); NMR: 5 9.64(1 H,似s )，7.8-7.7 (2H,m)，7.5-7.3 (4Η,ηι)，7·1-6.9 (5H，m)。 奮牖例2 (g) ( 4-[2-(4-氯笨磺醢胺基]-3-氯苯甲醢胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 50 39331 523506 A7 B7 五、發明説明（51(Please read the notes on the back before filling this page) TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.67 (chloroform: methanol: acetic acid = 1 7: 2 ·· 1); NMR: 5 9.64 (1 H, like s), 7.8-7.7 (2H, m), 7.5-7.3 (4Η, η), 7.1-6.9 (5H, m). Example 2 (g) (4- [2- (4-chlorobenzylsulfenylamino) -3-chlorobenzylamido] benzoic acid The paper size is applicable to China National Standard (CNS) A4 (210X297) %) 50 39331 523506 A7 B7 V. Description of the invention (51

COOH NMR (DMSO-d6) ： $ 12.8-12.6 (1H, br), 10.7-10.5 (1H, br), 10.12 (1H,s), 7.89 (2H, d), 7.7-7.5 (6H, m), 7.5-7.3 (3H, m)〇 實施例2 (h) 4-[2-(2-氛苯磺釀胺基）-5-氣苯甲醢胺基]苯甲酸COOH NMR (DMSO-d6): $ 12.8-12.6 (1H, br), 10.7-10.5 (1H, br), 10.12 (1H, s), 7.89 (2H, d), 7.7-7.5 (6H, m), 7.5-7.3 (3H, m). Example 2 (h) 4- [2- (2-Aminobenzenesulfonylamino) -5-gas benzamidineamino] benzoic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH TLC : R f 0.16 (氯仿：甲醇=9 : 1); NMR (DMSO-d6) ： 5 12.78 (1H, br), 10.80 (2H, br), 8.08-8.03 (1H, m),7.95 (2H, d), 7.88 (1H, d), 7.80 (2H, d), 7.66-7.46 (4H, m), 7.38 (1H, d)〇 經濟部中央標準局員工消費合作社印製 啻淪例2 ( η 4-[2-(3-氯苯磺醢胺基）-5-氯苯甲醢胺基')苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 51 3933 1 523506 A7 B7 五、發明説明备2COOH TLC: R f 0.16 (chloroform: methanol = 9: 1); NMR (DMSO-d6): 5 12.78 (1H, br), 10.80 (2H, br), 8.08-8.03 (1H, m), 7.95 (2H , d), 7.88 (1H, d), 7.80 (2H, d), 7.66-7.46 (4H, m), 7.38 (1H, d). Example 2 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (η 4- [2- (3-Chlorobenzenesulfonylamino) -5-chlorobenzylamine ') benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X297 mm) 51 3933 1 523506 A7 B7 V. Description of Invention 2

COOH TLC : Rf 0.15 (氯仿：甲醇=9:1); NMR (DMSO-d^) ： 5 12.76 (1 H, br), 10.62 (1H, brs), 10.36 (1 H, brs), 7.92 (2Η, d), 7.77-7.73 (4H, m), 7.67-7.44 (4H, m), 7.28 (1H, d)〇 置_]&例2 m 4-[2-(4-氯苯磺釀胺基）-5-氟苯甲醸胺基]苯甲酸COOH TLC: Rf 0.15 (chloroform: methanol = 9: 1); NMR (DMSO-d ^): 5 12.76 (1 H, br), 10.62 (1H, brs), 10.36 (1 H, brs), 7.92 (2Η , d), 7.77-7.73 (4H, m), 7.67-7.44 (4H, m), 7.28 (1H, d) 〇 __ & Example 2 m 4- [2- (4-chlorobenzenesulfonamide ) -5-fluorobenzylamino] benzoic acid

(請先閱讀背面之注意事項再填寫本頁) .COOH 〇(Please read the notes on the back before filling this page) .COOH 〇

II T L C ： R f 0.28 (氯仿：甲醇=17:3); 經濟部中央標準局員工消費合作社印製 NMR (DMSO-d^) ： ^ 12.78 (1H, brs), 10.50 (1H, s), 10.09 (1H, s), 7.95 (2H, d), 7.75 (2H, d), 7.68-7.26 (7H, m)〇 奮）fe例2 (k) 4-[2-(4 -氯苯磺釀胺基）-5-溴苯甲釀胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 52 3933 1II TLC: R f 0.28 (chloroform: methanol = 17: 3); NMR (DMSO-d ^) printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: ^ 12.78 (1H, brs), 10.50 (1H, s), 10.09 (1H, s), 7.95 (2H, d), 7.75 (2H, d), 7.68-7.26 (7H, m)) Example 2 (k) 4- [2- (4-chlorobenzenesulfonamide Based) -5-bromobenzylamine] benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X 297 mm) 52 3933 1

523506 A7 B7 五、發明説明“523506 A7 B7 V. Description of the invention "

COOH τ L c : R f 0.28 (氯仿：甲醇=17:3); NMR (DMSO-d^) ： δ 12.74 (1H, brs), 10.61 (1H, s), 10.33 (1H, s), 7.95 (2H, d)，7·89 (1H，d), 7.81-7.65 (5H, m), 7.53 (2H, d)，7.29 (1H, d)。COOH τ L c: R f 0.28 (chloroform: methanol = 17: 3); NMR (DMSO-d ^): δ 12.74 (1H, brs), 10.61 (1H, s), 10.33 (1H, s), 7.95 ( 2H, d), 7.89 (1H, d), 7.81-7.65 (5H, m), 7.53 (2H, d), 7.29 (1H, d).

WLMJSL2JJLL 4-[2-(4-氯苯磺釀胺基）-5-甲氧基苯甲醢胺基]苯甲酸 ------------ (請先閱讀背面之注意事項再填寫本頁)WLMJSL2JJLL 4- [2- (4-chlorobenzenesulfonylamino) -5-methoxybenzylamino] benzoic acid ------------ (Please read the precautions on the back first (Fill in this page again)

COOH 訂 T L C : R f 0.30 (氯仿：甲醇=17:3); 經濟部中央標準局員工消費合作社印製 NM R (DMSO-d6) ： 5 12.77 (1H, brs), 10.39 (1H, s), 9.79 (1 Η, s), 7.94 (2Η, d), 7.73 (2H, d), 7.59 (2H, d), 7.43 (2H, d), 7.25-7.15 (2H, m), 7.09 (1H, dd)〇 m m m 2(m) { 4-[2-(4-溴苯磺釀胺基）-5-氯苯甲醢胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 53 3933 1 523506 A7 B7 五、發明説明纟4 )COOH order TLC: R f 0.30 (chloroform: methanol = 17: 3); NM R (DMSO-d6) printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: 5 12.77 (1H, brs), 10.39 (1H, s), 9.79 (1 Η, s), 7.94 (2Η, d), 7.73 (2H, d), 7.59 (2H, d), 7.43 (2H, d), 7.25-7.15 (2H, m), 7.09 (1H, dd ) 〇mmmm 2 (m) {4- [2- (4-Bromobenzenesulfonylamino) -5-chlorobenzylamine] benzoic acid The paper size is applicable to China National Standard (CNS) A4 (210X297) (Centi) 53 3933 1 523506 A7 B7 V. Description of the invention 纟 4)

COOH NMR (DMS〇-d6) : 5 12.74 (1H，br),10.55(1 H，brs),10.27(1 H，brs)，7.92 (2H，d), 7.75-7.71 (3H，m)，7.66-7.51 (5H, m), 7·31 (1H，d)。 奮淪锎2 (n) 4 - [2-(4-甲基笨磺釀胺基）-5-氛苯甲醢胺基]苯甲酸COOH NMR (DMS〇-d6): 5 12.74 (1H, br), 10.55 (1 H, brs), 10.27 (1 H, brs), 7.92 (2H, d), 7.75-7.71 (3H, m), 7.66 -7.51 (5H, m), 7.31 (1H, d). Fenbin 2 (n) 4-[2- (4-methylbenzylsulfonylamino) -5-benzylbenzylamino] benzoic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH T L C : R f 0.30 (氯仿：甲醇=9 : 1); 經濟部中央標準局員工消費合作社印製 NMR (DMS〇-d6) : 5 12.76(1 H，br)，10.56(1 H，brs)，10.23(1 Η, brs)，7.93 (2H, d), 7.77-7.73 (3H, m), 7.60-7.51 (3H, m), 7.36 (1H, d), 7.23 (2H, d), 2.24 (3H, s)。 啻淪俐2 、 4-[2-(4-甲氧基笨磺醢胺基）-5-氯苯甲醢胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 54 3933 1 523506 A7 B7 五、發明説明)COOH TLC: R f 0.30 (chloroform: methanol = 9: 1); NMR (DMS〇-d6) printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: 5 12.76 (1 H, br), 10.56 (1 H, brs) , 10.23 (1 Η, brs), 7.93 (2H, d), 7.77-7.73 (3H, m), 7.60-7.51 (3H, m), 7.36 (1H, d), 7.23 (2H, d), 2.24 ( 3H, s). Benilin 2, 4- [2- (4-methoxybenzylsulfonylamino) -5-chlorobenzylamido] benzoic acid This paper is sized to the Chinese National Standard (CNS) A4 (210X297 mm) ) 54 3933 1 523506 A7 B7 V. Description of the invention)

NMR (DMSO-d6) ： 12.76(1H, br), 10.57(1H,brs), 10.16(1H,brs), 7.93 (2H, d), 7.77-7.73 (3H, m), 7.62 (2H, d), 7.59-7.52 (1H, m), 7.37 (1H, d), 6.93 (2H,d), 3.70 (3H，s)。 審嬾锎2 f D) 4-[2-(4-硝基苯磺醢胺基）-5-氣笨甲醸胺基]笨甲酸 (請先閱讀背面之注意事項再填寫本頁)NMR (DMSO-d6): 12.76 (1H, br), 10.57 (1H, brs), 10.16 (1H, brs), 7.93 (2H, d), 7.77-7.73 (3H, m), 7.62 (2H, d) , 7.59-7.52 (1H, m), 7.37 (1H, d), 6.93 (2H, d), 3.70 (3H, s). Review lazy 2 f D) 4- [2- (4-Nitrobenzenesulfonylamino) -5-phenylbenzylamino] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印II NMR (DMSO-d^) ： 12.71 (1H, br), 10.55-10.35 (2H, br), 8.19 (2H, d), 7.93-7.86 (4H, m), 7.71-7.64 (3H, m), 7.58-7.52 (1H, m), 7.32 (1H, d)〇 啻牖例2 (、 4-[2-(2,4-二氛苯磺釀胺基）-5-氯苯甲醢胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 55 39331 523506 A7 B7Printed by the Consumer Standards of the Central Bureau of Standards, Ministry of Economic Affairs II NMR (DMSO-d ^): 12.71 (1H, br), 10.55-10.35 (2H, br), 8.19 (2H, d), 7.93-7.86 (4H, m), 7.71-7.64 (3H, m), 7.58-7.52 (1H, m), 7.32 (1H, d). Example 2 (, 4- [2- (2,4-dioxobenzenesulfonylamino)- 5-Chlorobenzamidine] benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X 297 mm) 55 39331 523506 A7 B7

五、發明説明<b6 )V. Description of the invention < b6)

C〇〇H NMR (DMSO-d6) ： 12.50 (1H, br), 10.73 (2H, br), 7.99-7.91 (3H, m), 7.85 (1H,似 d )，7.79-7.71 (3H，m), 7.58-7.51 (2H，m), 7.36 (1H, d)。 "SLM m 2 (Γ) 4-[2-(4-丁基苯磺醸胺基）-5-氯苯甲釀胺基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)COH NMR (DMSO-d6): 12.50 (1H, br), 10.73 (2H, br), 7.99-7.91 (3H, m), 7.85 (1H, like d), 7.79-7.71 (3H, m) , 7.58-7.51 (2H, m), 7.36 (1H, d). " SLM m 2 (Γ) 4- [2- (4-Butylbenzenesulfonylamino) -5-chlorobenzylamino] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 T L C : R f 0.33 (氯仿：甲醇=9 ·· 1); NMR (DMSO-d^) ： 5 12.72 (1H, br), 10.55 (1H, brs), 10.24 (1H, s), 7.92 (2H, d), 7.78-7.72 (3H, m), 7.60 (2H, d), 7.57-7.51 (1H, m), 7.37 (1H, d), 7.24 (2H, d), 2.54 -2.49 (2H, m)，1.48-1.33 (2H, m), 1.29-1 ·11 (2H, m), 0.82 (3H, t)。 y麻锎2 ( s ) 4-[2-(4-氯苯磺醢胺基）苯甲釀胺基]苯伊酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 56 3933 1 523506 A7 B7 五Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.33 (chloroform: methanol = 9 ·· 1); NMR (DMSO-d ^): 5 12.72 (1H, br), 10.55 (1H, brs), 10.24 (1H, s), 7.92 (2H, d), 7.78-7.72 (3H, m), 7.60 (2H, d), 7.57-7.51 (1H, m), 7.37 (1H, d), 7.24 (2H, d ), 2.54 -2.49 (2H, m), 1.48-1.33 (2H, m), 1.29-1 · 11 (2H, m), 0.82 (3H, t). y Mochi 2 (s) 4- [2- (4-Chlorobenzenesulfonylamino) benzylamine] benzylic acid The paper size is applicable to China National Standard (CNS) A4 (210X297 mm) 56 3933 1 523506 A7 B7 five

、發明説明“, Invention description "

COOH τ L c : R f 0.30 (己烷：乙酸乙酯··乙酸=16:7:1); NMR (DMSO-d^) ： 5 13.00-12.60 (1H, brs), 10.55 (1H, brs), 10.38 (1H, brs), 7.95 (2H, d), 7.78 (2H, d), 7.74 (1 H, m), 7.72 (2H, d), 7.51 (2H, d), 7.50 (1H, m), 7.40-7.24 (2H, m)〇 (請先閲讀背面之注意事項再填寫本頁) 奩_锎2 (t ) 4- (2-苯磺醸胺基COOH τ L c: R f 0.30 (hexane: ethyl acetate · acetic acid = 16: 7: 1); NMR (DMSO-d ^): 5 13.00-12.60 (1H, brs), 10.55 (1H, brs) , 10.38 (1H, brs), 7.95 (2H, d), 7.78 (2H, d), 7.74 (1 H, m), 7.72 (2H, d), 7.51 (2H, d), 7.50 (1H, m) , 7.40-7.24 (2H, m) 〇 (Please read the precautions on the back before filling this page) 奁 _ 锎 2 (t) 4- (2-benzenesulfonamido

氟苯甲醢胺基）苯甲酸 COOHFluorobenzylamino) benzoic acid COOH

經濟部中央標準局員工消費合作社印製 NMR (DMSO-d6) ： 5 12.70 (1H,br), 10.52 (1H, br), 10.13 (1H, br), 7.92 (2H, d), 7.74 (2H, d), 7.68-7.64 (2H, m), 7.59-7.27 (6H, m)〇 2 ("u 丄 4-(2-笨磺釀胺基氟苯甲醢胺基）苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210x297公釐） 5 7 3933 1 523506 A7 B7 五、發明説明$8NMR (DMSO-d6) printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: 5 12.70 (1H, br), 10.52 (1H, br), 10.13 (1H, br), 7.92 (2H, d), 7.74 (2H, d), 7.68-7.64 (2H, m), 7.59-7.27 (6H, m) 〇2 (" u 丄 4- (2-benzylsulfonylaminobenzylamino) benzoic acid This paper is suitable for paper size China National Standard (CNS) A4 specification (210x297 mm) 5 7 3933 1 523506 A7 B7 V. Invention description $ 8

^^C〇〇HXT Γ 'ΝΗ S〇2 Ό τ L C ： R f 0.20 (氯仿：甲醇= 9:1); NMR (DMSO-d6) ： 5 12.81 (1H, br), 10.85 (1H, br), 10.60 (1H, br), 7.95-7.74 (7H, m), 7.63-7.46 (3H, m), 7.19-7.02 (2H, m)〇 奮 m m 2 (v)4-[2-(4-氯苯磺醢胺基）-4-氟苯甲醸胺基]苯甲酸 r^YC00H Η 'ΝΗ S〇2^^ C〇〇HXT Γ 'ΝΗ S〇2 Ό τ LC: R f 0.20 (chloroform: methanol = 9: 1); NMR (DMSO-d6): 5 12.81 (1H, br), 10.85 (1H, br) , 10.60 (1H, br), 7.95-7.74 (7H, m), 7.63-7.46 (3H, m), 7.19-7.02 (2H, m) 〇fen mm 2 (v) 4- [2- (4-chloro Benzenesulfonylamino) -4-fluorobenzylamino] benzoic acid r ^ YC00H Η 'ΝΗ S〇2

Cl (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 TLC : R f 0.22 (氯仿：甲醇= 9:1); NMR (DMSO-d^) ： 5 12.28 (1H, br), 10.75 (1H, br), 10.58 (1H, br), 7.95-7.72 (7H, m), 7.53 (2H, d), 7.19-7.08 (2H, m)〇 w m m 2 (w)4-[2-(4-氟苯磺醢胺基）-5-氯苯甲釀胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 58 39331 523506 A7 B7Cl (Please read the notes on the back before filling this page) TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.22 (chloroform: methanol = 9: 1); NMR (DMSO-d ^): 5 12.28 ( 1H, br), 10.75 (1H, br), 10.58 (1H, br), 7.95-7.72 (7H, m), 7.53 (2H, d), 7.19-7.08 (2H, m) 〇wmm 2 (w) 4 -[2- (4-Fluorobenzenesulfonylamino) -5-chlorobenzylamino] benzoic acid The paper size applies to the Chinese National Standard (CNS) A4 specification (210X297 mm) 58 39331 523506 A7 B7

五、發明説明“）5. Description of the invention ")

COOH NMR (DMSO-dg) ： δ 12.75 (1Η, br), 10.58 (1H, br), 10.27 (1H, brs), 7.93 (2H, d), 7.80-7.72 (5H, m), 7.54 (1H, dd), 7.34-7.22 (3H, m)〇 g施锎2 (xl_ 4-[2-(4-三氟甲基苯磺醸胺基氯苯甲醯胺基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)COOH NMR (DMSO-dg): δ 12.75 (1Η, br), 10.58 (1H, br), 10.27 (1H, brs), 7.93 (2H, d), 7.80-7.72 (5H, m), 7.54 (1H, dd), 7.34-7.22 (3H, m) 0 g Shi 2 (xl_ 4- [2- (4-trifluoromethylbenzenesulfonylaminochlorobenzylamino) benzoic acid (Please read the (Please fill in this page again)

經濟部中央標準局員工消費合作社印製 T L C ： R f 0.26 (氛仿：甲醇= 9:1); NMR (DMSO-d0) ： δ 12.70 (1Η, br), 10.56 (1H, br), 10.41 (1H, br), 7.92-7.68 (9H, m), 7.54(1 H,似 dd ), 7.31 (1H，d)。 _ 例 2 ( y i 4-(2-苯磺釀胺基-5-氯苯甲釀胺基甲基）苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210χ 297公釐） 59 3933 1 523506 A7 B7 五、發明説明（60 ) 〇TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.26 (Diffuse: Methanol = 9: 1); NMR (DMSO-d0): δ 12.70 (1Η, br), 10.56 (1H, br), 10.41 ( 1H, br), 7.92-7.68 (9H, m), 7.54 (1 H, like dd), 7.31 (1H, d). _ Example 2 (yi 4- (2-benzenesulfonylamino-5-chlorobenzylaminomethyl) benzoic acid This paper is sized to the Chinese National Standard (CNS) A4 (210 × 297 mm) 59 3933 1 523506 A7 B7 V. Description of the invention (60) 〇

T L C ： R f 0.45 (氛仿：甲醇=4:1); NMR (DMSO-d^) 12.90(1H,s),11.47(1H,s), 9.46(1 H,t), 7.94 (2H,d), 7.86 (1H, d), 7.77-7.36 (9H, m), 4.48 (1H, d)〇 奮遍俐2 f 7·) 4-[2-(2-笨基乙烯基）磺醸胺基氯苯甲醢胺基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)TLC: R f 0.45 (methanol: 4: 1); NMR (DMSO-d ^) 12.90 (1H, s), 11.47 (1H, s), 9.46 (1 H, t), 7.94 (2H, d ), 7.86 (1H, d), 7.77-7.36 (9H, m), 4.48 (1H, d) 〇 Fenbali 2 f 7 ·) 4- [2- (2-benzylvinyl) sulfonamido Chlorobenzylamine] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 NMR(CD3OD) : 7.98 (2H, d), 7.83 (1H, d), 7.72 (2H, d), 7.63 (1H, d), 7.53 (1H, dd), 7.5-7.2 (6H, m), 7.01 (1H，d)。NMR (CD3OD) printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: 7.98 (2H, d), 7.83 (1H, d), 7.72 (2H, d), 7.63 (1H, d), 7.53 (1H, dd), 7.5-7.2 (6H, m), 7.01 (1H, d).

n m m 2( a a I 4-[2-(2 -苯基乙基）磺醢胺基-5-氯笨甲醸胺基]苯甲酸n m m 2 (a a I 4- [2- (2-phenylethyl) sulfonamido-5-chlorobenzylamido] benzoic acid

本紙張尺度適用中國國家標準（CNS ) A4規格（210x297公羞） 60 3933 1 523506 A7 B7 五、發明説明（61 ) T L C : R f 0.27 (氯仿··甲醇=9 : 1 ); NMR (DMSO-dfe) ： 5 12.75 (1H, br), 10.78 (1H, brs), 10.05 (1H, s), 7.95-7.79 (5H, m), 7.63-7.53 (2H, m), 7.24-7.10 (5H, m), 3.53-3.45 (2H, m), 2.99-2.91 (2H, m)〇 奮牖例2 (bb) 4-[2-(4-氯苯磺醢胺基）-5-硝基苯甲醢胺基]苯甲酸This paper size applies Chinese National Standard (CNS) A4 specification (210x297), 60 3933 1 523506 A7 B7 V. Description of the invention (61) TLC: R f 0.27 (chloroform ·· methanol = 9: 1); NMR (DMSO- dfe): 5 12.75 (1H, br), 10.78 (1H, brs), 10.05 (1H, s), 7.95-7.79 (5H, m), 7.63-7.53 (2H, m), 7.24-7.10 (5H, m ), 3.53-3.45 (2H, m), 2.99-2.91 (2H, m). Example 2 (bb) 4- [2- (4-chlorobenzenesulfonylamino) -5-nitrobenzidine Amine] benzoic acid

^^C〇〇HXT^^ C〇〇HXT

'N Η NH 〇2S\ Ιλ'N Η NH 〇2S \ Ιλ

Cl TLC ： R f 0.32 (己烷：乙酸乙酯：乙酸=12:4:1);. NMR (DMSO-d^) 12.50-10.00 (2H, brs), 8.66 (1H, d), 8.36-8.24 (1H, dd), 8.05-7.87 (4H, m), 7.80 (2H, d), 7.68-7.55 (3H, m)〇 啻施例34-[2-(4-羥基苯磺醢胺基卜5-氯苯甲醢胺基]苯甲酸 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印mCl TLC: R f 0.32 (hexane: ethyl acetate: acetic acid = 12: 4: 1) ;. NMR (DMSO-d ^) 12.50-10.00 (2H, brs), 8.66 (1H, d), 8.36-8.24 (1H, dd), 8.05-7.87 (4H, m), 7.80 (2H, d), 7.68-7.55 (3H, m). Example 34- [2- (4-Hydroxybenzenesulfonamide) 5 -Chlorobenzamidine] benzoic acid (Please read the notes on the back before filling this page) Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

OH 4-[2-(4-三甲基乙釀基氧基笨磺醢胺基）-5-氯苯甲酿 胺基]苯甲酸甲酶（214mg，依參考例1、2及3及實施例1之 相同操作而合成）之甲酵-THF(8h1+3bi1)混合溶液中，添加 本紙張尺度適用中國國家標準（CNS ) A4規格（21〇'乂297公釐） 61 3933 1 523506 A7 B7 五、發明説明（62 ) 2N氫氧化納水溶液（2ib1),在60t!攪拌1天。反應液中添加 塩酸後，Μ乙酸乙酯萃取。有機層予Μ洗淨，乾燥，由甲 醇-乙酸乙酷-己烷之混合溶劑中再结晶而純化，得到具下 列物理數據之標題化合物（105mg)。 TLC ： Rf 0.42(氯仿：甲酵：乙酸=45:4:1); HMR(DMS0-d6): δ13·0鐘12,6(lH,br), 10·64(1Η,似 s), 10·50(1Η,似 s), 10.21(lH,s), 7.95(2H,d), 7·9-7·7(3Η ,m) , 7·6-7·3 (4H , m) , 6·76 (2H , d) 參者例4 4-[2-(2-硝基-5-氯苯基）-(ΕΖ)-乙烯基]苯甲酸甲_ (請先閱讀背面之注意事項再填寫本頁)OH 4- [2- (4-trimethylethyloxybenzylsulfonylamino) -5-chlorobenzylamino] benzoic acid enzyme (214mg, according to Reference Examples 1, 2 and 3 and implementation In the same solution as in Example 1), a formic acid-THF (8h1 + 3bi1) mixed solution was added to the paper standard applicable to the Chinese National Standard (CNS) A4 specification (21〇'297 mm) 61 3933 1 523506 A7 B7 V. Description of the invention (62) 2N sodium hydroxide aqueous solution (2ib1), stir at 60t! For 1 day. After adding osmic acid to the reaction solution, it was extracted with ethyl acetate. The organic layer was washed with M, dried, and purified by recrystallization from a mixed solvent of methanol-ethyl acetate-hexane to obtain the title compound (105 mg) having the following physical data. TLC: Rf 0.42 (chloroform: formazan: acetic acid = 45: 4: 1); HMR (DMS0-d6): δ13 · 0 clock 12,6 (lH, br), 10.64 (1Η, like s), 10 50 (1Η, like s), 10.21 (lH, s), 7.95 (2H, d), 7.9-7 · 7 (3Η, m), 7.6 ~ 7.3 (4H, m), 6 · 76 (2H, d) Participant Example 4 4- [2- (2-Nitro-5-chlorophenyl)-(EZ) -vinyl] benzoic acid _ (Please read the precautions on the back before filling (This page)

經濟部中央標準局員工消費合作社印製 4-甲氧羰基苯基甲基三笨基磺醸溴（4.83g)之THF(20 ml )溶液中，添加第三丁酵鉀（600 mg),於室溫攪拌1小時 ，在0¾下，添加2 -硝基-5 -氯笨甲醛（742nig),在室溫搅 拌30分鐘後，反應混合物中注入稀塩酸。K己烷-乙酸乙 酯萃取，有機層予Μ洗淨、乾燥並減壓濃縮。殘留物K矽 膠管柱層析法（己烷-乙酸乙酯）純化，由己烷-乙酸乙_之 混合溶劑再结晶而純化，得具下列物理數據之標題化合物 (6 8 0 m g ) 〇 TLC: Rf 0.44(己烷：乙酸乙 _=4:1) 參者例5 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 62 393 3 1 523506 A7 B7 五、發明説明（63 ) 4-[2-(2_胺基-5-氯笨基）-(E)-乙烯基]苯甲酸甲醣及 4-[2-(2-胺基-5-氯苯基）-(Z)_乙烯基]苯甲酸甲酯To the solution of 4-methoxycarbonylphenylmethyltribenzylsulfonium bromide (4.83g) in THF (20 ml) printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs was added potassium tert-butyrate (600 mg). After stirring at room temperature for 1 hour, 2-nitro-5 -chlorobenzaldehyde (742nig) was added at 0¾, and after stirring at room temperature for 30 minutes, dilute acetic acid was poured into the reaction mixture. K-hexane-ethyl acetate extraction, the organic layer was washed with MgSO, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) and recrystallized from a mixed solvent of hexane-ethyl acetate to obtain the title compound (680 mg) with the following physical data.TLC: Rf 0.44 (Hexane: ethyl acetate_ = 4: 1) Participant Example 5 The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 62 393 3 1 523506 A7 B7 V. Description of the invention (63) 4 -[2- (2-Amino-5-chlorobenzyl)-(E) -vinyl] benzoic acid xylose and 4- [2- (2-amino-5-chlorophenyl)-(Z) _Vinyl] methyl benzoate

4-[2-(2-硝基-5-氯苯基）-(EZ)-乙烯基]苯甲酸甲_ (525mg;由參考例4合成）之THF(4ir1)溶液中添加水（1.5b1 )、2N塩酸及邐原嫌（554ng),於室溫攪拌隔夜。再添加2N 塩酸（0.2ml)及遷原鐵粉（330ag),攪拌3天。反應混合物 K乙酸乙酷稀釋後過濾。濾液予Μ洗淨、乾燥及減壓灞縮 。殘留物Μ矽膠管柱層析法（乙醚-己烷-乙酸乙酯）純化， 得到具下列物理數據之標題化合物。 (Ε)型 TLC: Rf 0.37(乙酸乙 _ :苯=5:95) 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) (Z)型 1^(：:1^0.41(乙酸乙酯：苯=5:95) 奮_例4 ' 4-[2-[2-(4-氯苯磺醢胺基）-5-氯笨基]-(E)-乙烯基]苯甲 酸甲簾 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 63 3933 1 523506 A7 B74- [2- (2-Nitro-5-chlorophenyl)-(EZ) -vinyl] benzoate (525 mg; synthesized from Reference Example 4) in THF (4ir1) was added with water (1.5b1 ), 2N osmic acid and yakihara (554ng), stir overnight at room temperature. Add 2N osmic acid (0.2ml) and Qianyuan iron powder (330ag) and stir for 3 days. The reaction mixture was diluted with ethyl acetate and filtered. The filtrate was washed with M, dried and shrunk under reduced pressure. The residue M was purified by silica gel column chromatography (diethyl ether-hexane-ethyl acetate) to give the title compound with the following physical data. (Ε) type TLC: Rf 0.37 (ethyl acetate_: benzene = 5: 95) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling this page) (Z) type 1 ^ (: : 1 ^ 0.41 (ethyl acetate: benzene = 5: 95) Fen_Example 4 '4- [2- [2- (4-chlorobenzenesulfonylamino) -5-chlorobenzyl]-(E)- Vinyl] formyl benzoate This paper is sized for China National Standard (CNS) A4 (210X297 mm) 63 3933 1 523506 A7 B7

(請先閲讀背面之注意事項再填寫本頁) (130ag;由參考例5合成）之二氯甲烷（3ml)溶液中，添加 吡啶（0.073juA)及對-氯苯磺醯氯，於室溫下攪 拌隔夜。反應混合物中注入稀塩酸，以乙酸乙酯萃取。有 機層予Μ洗淨、乾煉及減壓濃縮。殘留物以矽膠管柱曆析 法（乙酸乙酯-己烷）純化，得到具下列物理數據之標題化 合物（205iag)。 仉(：：1^0.15(乙酸乙酯：笨=4:96); NMR:58.02(2H，d),7.63(2H,d),7.51(lH,s)，7.41-7·30(4Η，·), 7·26-7·22(2Η,πι)，6.91(lH，d), 6.81(lH，d ),6-63(lH,s), 3.95 (3H,s) V m m A(^) 經濟部中央標準局員工消費合作社印製 4-[2-[2-(4-氯苯磺醯胺基）-5-氯笨基]-(Z)-乙烯基]苯甲 酸甲酯(Please read the precautions on the back before filling this page) (130ag; synthesized from Reference Example 5) in dichloromethane (3ml) solution, add pyridine (0.073juA) and p-chlorobenzenesulfonyl chloride, at room temperature Stir overnight. The reaction mixture was poured into dilute acetic acid and extracted with ethyl acetate. The organic layer was washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-hexane) to give the title compound (205iag) with the following physical data.仉 (:: 1 ^ 0.15 (ethyl acetate: benzine = 4: 96); NMR: 58.02 (2H, d), 7.63 (2H, d), 7.51 (lH, s), 7.41-7 · 30 (4Η, ·), 7.26-7 · 22 (2Η, πm), 6.91 (lH, d), 6.81 (lH, d), 6-63 (lH, s), 3.95 (3H, s) V mm A (^ ) 4- [2- [2- (4-chlorobenzenesulfonylamino) -5-chlorobenzyl]-(Z) -vinyl] benzoic acid methyl ester printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

使用參考例5所合成之Z體，如實施例4般相同操作， 得到具下列物理數據之標題化合物。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 64 3933 1Using the Z body synthesized in Reference Example 5, the same operation as in Example 4 was performed to obtain the title compound with the following physical data. This paper size applies to China National Standard (CNS) A4 (210X297 mm) 64 3933 1

02S 523506 A7 B7 五、發明説明（65) TLC:Rf0.23(Z_Z_:，=4:96) NMR： δ 7.82(2Η , d) , 7 · 57(2Η , d) , 7 . 46 (1 Η,d) , 7.33( 2H,d)， 7.24(lH,dd), 7.06(lH,d), 6.99(2H,d)， 6·72( lH,d), 6.48(lH,s), 6.20(lH,d), 3.90(3H,s) 奮_例5 4-[2-[2-(4-氯苯磺醯胺基）-5-氯苯基]-(E)-乙烯基]苯甲 酸02S 523506 A7 B7 V. Description of the invention (65) TLC: Rf0.23 (Z_Z _:, == 4:96) NMR: δ 7.82 (2Η, d), 7.57 (2Η, d), 7.46 (1 Η , d), 7.33 (2H, d), 7.24 (lH, dd), 7.06 (lH, d), 6.99 (2H, d), 6.72 (lH, d), 6.48 (lH, s), 6.20 ( lH, d), 3.90 (3H, s) Fen_Example 5 4- [2- [2- (4-chlorobenzenesulfonamido) -5-chlorophenyl]-(E) -vinyl] benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

使用4-[2-[2-(4-氯苯磺醢胺基）-5-氯苯基]-(E)-乙 烯基]苯甲酸甲酯（190mg;由實施例4合成），如實施例2般 操作，得到具下列物理數據之標題化合物（168iig)。 TLC: Rf 0.36(氯仿：甲醇=17:3);Using methyl 4- [2- [2- (4-chlorobenzenesulfonamido) -5-chlorophenyl]-(E) -vinyl] benzoate (190 mg; synthesized from Example 4), as implemented Following the procedure of Example 2, the title compound (168iig) was obtained with the following physical data. TLC: Rf 0.36 (chloroform: methanol = 17: 3);

NMR (DMSO-de) ： δ 10 · 11 (1 Η , brs ) , 7.96(2H,d), 7.80(1H 經濟部中央標準局員工消費合作社印製 ，d), 7.59(2H,d), 7·52-7,41(4Η,πι), 7.36(lH,dd), 7 . 20 (1H , d) , 7 . 15 (1H , d) , 7 · 08 (1H,d) 奮_例5 (a) 〈 4 - [2-[2-(4-氯笨磺釀胺基）-5-氯苯基]-(Z)-乙烯基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 65 3933 1 523506 A7 B7 五、發明説明（66 )NMR (DMSO-de): δ 10 · 11 (1 Η, brs), 7.96 (2H, d), 7.80 (1H Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs, d), 7.59 (2H, d), 7 52-7,41 (4Η, πι), 7.36 (lH, dd), 7.20 (1H, d), 7.15 (1H, d), 7.08 (1H, d) Fen_Example 5 ( a) <4-[2- [2- (4-chlorobenzylsulfonylamino) -5-chlorophenyl]-(Z) -vinyl] benzoic acid This paper is sized for China National Standard (CNS) A4 (210X297 mm) 65 3933 1 523506 A7 B7 V. Description of the invention (66)

COOH 使用實施例4(a)合成之4-[2-[2-(4-氯苯磺醢胺基）-5-氯苯基]-(Z)-乙烯基]笨甲酸甲酿，如實施例2般操作， 得到具下列物理數據之標題化合物。 TLC : Rf 0 . 46 (氯仿：甲酵=17 : 3); HMR (DMSO-de) ： δ 1 0 . 05 (1 Η , brs ) , 7 · 79 - 7 · 67 ( 4 Η , m), 7·55(2Η,(〇， 7.30(lH,dd), 7·15(1Η,(Π， 7·00(1Η,&lt;Π, 6 · 91 (1Η,d)，6.64 (2Η，s) 奮_例6 (請先閱讀背面之注意事項再填寫本頁)COOH 4- [2- [2- (4-chlorobenzenesulfonamido) -5-chlorophenyl]-(Z) -vinyl] benzyl formic acid synthesized in Example 4 (a), as implemented Following the procedure of Example 2, the title compound was obtained with the following physical data. TLC: Rf 0. 46 (chloroform: formazan = 17: 3); HMR (DMSO-de): δ 1 0. 05 (1 Η, brs), 7 · 79-7 · 67 (4 Η, m), 7.55 (2Η, (〇, 7.30 (lH, dd), 7.15 (1Η, (Π, 7.00 (1Η, &lt; Π, 6. · 91 (1Η, d), 6.64 (2Η, s) Fen_Example 6 (Please read the precautions on the back before filling this page)

4-[2-[2-(4-氯苯基）磺酿胺基-5-氯苯基]乙基]苯甲酸 COOH4- [2- [2- (4-chlorophenyl) sulfoamino-5-chlorophenyl] ethyl] benzoic acid COOH

經濟部中央標準局員工消費合作社印製Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

4-[2-[2-(4-氯笨基）磺醢胺基-5-氯苯基]乙烯基]苯 甲酸（54®g;由實施例5合成）之THF(4ml)溶液中添加氫氧 化鉛（3mg),在氫氣中室溫下攪拌2小時。遇濂反應混合物 ,濾液減壓濃縮。殘留物中添加二氯甲烷，攪拌，過濾收 集所生成之结晶，得到具下列物理數據之檷蘼化合物（ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 66 3933 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（67) 4 6 ffi g ) 〇 TLC: Rf 0.42(氯仿：甲醇=17:3); NMR(DMS0-d6): 512.75(lH,brs), 9.88(lH,s), 7·84( 2H，d)，7·72-7·57(4Η,ιε), 7.32(lH,d), 7.23(2H,d)· 7/18(lH,dd), 6.88(lH,d) 參者例6 4-(2-三氟乙醢胺基-5-氯苯氧甲基）苯甲酸甲簾 COOMe4- [2- [2- (4-chlorobenzyl) sulfonamido-5-chlorophenyl] vinyl] benzoic acid (54 g; synthesized from Example 5) was added to a solution of THF (4 ml) Lead hydroxide (3 mg) was stirred at room temperature under hydrogen for 2 hours. When the reaction mixture was encountered, the filtrate was concentrated under reduced pressure. Dichloromethane was added to the residue, stirred, and the resulting crystals were collected by filtration to obtain a pyrene compound with the following physical data (this paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 66 3933 1 523506 A7 B7 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. 5. Description of the invention (67) 4 6 ffi g) 〇 TLC: Rf 0.42 (chloroform: methanol = 17: 3); NMR (DMS0-d6): 512.75 (lH, brs ), 9.88 (lH, s), 7.84 (2H, d), 7.72-7 · 57 (4Η, ιε), 7.32 (lH, d), 7.23 (2H, d) · 7/18 (lH , dd), 6.88 (lH, d) Participant Example 6 4- (2-Trifluoroacetamido-5-chlorophenoxymethyl) benzoic acid formaldehyde COOMe

〇^CF3 2 -三氟乙醯胺基-5-氯苯酚（350ng)及4 -溴甲基苯甲酸 甲_(435ng)之DMF(3al)溶液中，在室溫下添加碳酸鉀（ 2 63ing),在60¾下搅拌1小時30分鐘。反應結束後，反應 混合物中注入冷稀塩酸，K乙酸乙_萃取。有機層予K洗 淨、乾煉並減壓濃縮。殘留物Μ矽膠管柱層析法（乙酸乙 酯苯）純化，得到具有下列物理數據之摞題化合物（ 353ag) Ο TLC: Rf 0.44(乙酸乙酯：苯=5:95) 參者例7 4-(2-胺基-5-氣苯氧基甲基）苯甲酸甲簾 XOOMe〇 ^ CF3 2-trifluoroacetamido-5-chlorophenol (350ng) and 4-bromomethylbenzoic acid methyl ester (435ng) in DMF (3al) solution, potassium carbonate (2 63ing ), Stirred at 60¾ for 1 hour and 30 minutes. After the reaction was completed, the reaction mixture was poured into cold dilute acetic acid and extracted with ethyl acetate. The organic layer was washed with K, dried and concentrated under reduced pressure. The residue M was purified by silica gel column chromatography (ethyl acetate benzene) to obtain the title compound (353ag) having the following physical data. TLC: Rf 0.44 (ethyl acetate: benzene = 5: 95) See Example 7 4 -(2-Amino-5-Gaphenoxymethyl) benzoic acid methyl curtain XOOMe

nr 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 67 3933 1 (請先閱讀背面之注意事項再填寫本頁) 523506 A7 B7 五、發明説明（68 ) 4 -（2-三氟乙醯胺基-5-氯苯氧甲基）苯甲酸甲_( 300flig,由參考例6合成）之THF -甲醇Uial + lOial)之混合溶 液中，添加碳酸納（440mg)之水（2ml)溶液，在60TC攪拌 8小時及在室溫授拌隔夜。反應混合物中注入稀塩酸，Μ 乙酸乙酯萃取。有機層予以洗淨、乾煉及減壓濃縮。殘留 物Κ矽膠管柱層析法（乙酸乙酯-苯）鈍化，得到具下列物 理數據之標題化合物（194ag)。 TLC: Rf 0.27(乙酸乙酯：苯=5:95) 奮_例7 4-[2-(4-氯苯磺醸胺基）-5-氯苯氧甲基]苯甲酸甲_ (請先閲讀背面之注意事項再填寫本頁)nr This paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 67 3933 1 (Please read the precautions on the back before filling out this page) 523506 A7 B7 V. Description of the invention (68) 4-(2- Trifluoroacetamido-5-chlorophenoxymethyl) benzoate (300flig, synthesized from Reference Example 6) in a THF-methanol Uial + lOial) mixed solution was added with sodium carbonate (440mg) of water ( 2ml) solution, stirred at 60TC for 8 hours and incubated overnight at room temperature. The reaction mixture was poured into dilute acetic acid, and extracted with ethyl acetate. The organic layer was washed, dried, and concentrated under reduced pressure. The residue was inactivated by silica gel column chromatography (ethyl acetate-benzene) to give the title compound (194ag) with the following physical data. TLC: Rf 0.27 (ethyl acetate: benzene = 5: 95) Fen_Example 7 4- [2- (4-chlorobenzenesulfonylamino) -5-chlorophenoxymethyl] benzoic acid_ (Please first (Read the notes on the back and fill out this page)

使用4-(2-胺基-5-氯笨氧甲基）笨甲酸甲酯（165iBg; 經濟部中央標準局員工消費合作社印製 由參考例7合成），如實施例4般相同操作，得到具下列物 理數據之標題化合物（2 59 mg)。 TLC: Rf 0.30(乙酸乙酷：苯=5:95); NMR： 58.06(2H,d), 7.59(2H,d), 7.53(lH,d), 7.34( 2H,d), 7.18(2H,d), 6.96(lH,dd), 6.82(lH,brs)· 6·76 (1H , d) , 4·89(2H,s) , 3·96 (3H , s) 奮施例7(a)_ 4-(2-苯磺藤胺基-4-氯苯氧甲基）苯甲酸甲酯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 68 3933 1 523506 A7 B7 五、發明説明（69 )Using 4- (2-amino-5-chlorobenzyloxymethyl) benzylcarboxylate (165iBg; printed by Reference Consumer Cooperative of Employees' Cooperative of Central Bureau of Standards of the Ministry of Economic Affairs), the same operation as in Example 4 was used to obtain The title compound (2 59 mg) with the following physical data. TLC: Rf 0.30 (ethyl acetate: benzene = 5: 95); NMR: 58.06 (2H, d), 7.59 (2H, d), 7.53 (lH, d), 7.34 (2H, d), 7.18 (2H, d), 6.96 (lH, dd), 6.82 (lH, brs), 6.76 (1H, d), 4.89 (2H, s), 3.96 (3H, s) Example 7 (a) _ Methyl 4- (2-benzenesulfenylamino-4-chlorophenoxymethyl) benzoate This paper is sized for China National Standard (CNS) A4 (210X297 mm) 68 3933 1 523506 A7 B7 V. Invention Instructions (69)

CICI

NH 02S Ό COOMe 使用2-三氟乙醢胺基-4-氯苯酚，如參考例64參考例 74實施例44實施例2般相同操作，得到具下列物理數據 之標題化合物。 TLC: Rf 0.37(己烷：乙酸乙酯=2:1); NMR: S8.01(2H,d,J=8,4Hz), 7.75(2H,a), 7.63(lH,d, 』= 2·4Ηζ), 7·56(1Η,ιβ), 7·43(2Η,ιβ), 7.15(2H,d,J = 8.4 Hz), 6.69(lH,brs), 6·97(1Η,άυ = 2·4,8·8Ηζ), 6·63( lH,d,J=8.8Hz), 4.92(2H,s), 3.94(3H,s) 直―例&amp; (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 磺cl 苯 氯 -NH 02S Ό COOMe was carried out in the same manner as in Reference Example 64, Reference Example 74, Example 44 and Example 2 to obtain the title compound having the following physical data. TLC: Rf 0.37 (hexane: ethyl acetate = 2: 1); NMR: S8.01 (2H, d, J = 8,4Hz), 7.75 (2H, a), 7.63 (lH, d, ′ = 2 4Ηζ), 7.56 (1Η, ιβ), 7.43 (2Η, ιβ), 7.15 (2H, d, J = 8.4 Hz), 6.69 (lH, brs), 6.97 (1Η, άυ = 2 · 4,8 · 8Ηζ), 6.63 (lH, d, J = 8.8Hz), 4.92 (2H, s), 3.94 (3H, s) Straight Example &amp; (Please read the precautions on the back before filling (This page) Sulfocl benzene chloride printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs-

苯 TJ 酸 甲 使用4-[2-(4-氯苯磺醱胺基）-5-氯苯氧甲基]笨甲酸 甲酷（21 Omg ;由實施例7合成），如實施例2般相同操作， 得到具下列物理數據之標題化合物（197mg)。 TLC: Rf 0.43(氯仿：甲酵=17:3); 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 69 3 9 3 3 1 523506 A7 B7 五、發明説明（70) NMR (DMSO-de) ： δ 9·89 (1H , brs) , 7 . 93 (2H , d) , 7 . 6 0 ( 2 H, d), 7,42(2H，d), 7.34(2H,d), 7.29(lH,d)， 7.06(lH,d) ,7·01 (lH,dd) , 4.98(2H,s) 奮 _ 例 8 (a) -8 (p) 如參考例6、7及實施例7及8般相同操作，得到具有下 列物理數據之標題化合物。 窨_ _例8 (a) 4-(2-苯磺醯胺基-5-氯苯氧甲基）苯甲酸 (請先閲讀背面之注意事項再填寫本頁)Benzyl TJ acid methyl 4- [2- (4-chlorobenzenesulfonamido) -5-chlorophenoxymethyl] benzylcarboxylate (21 Omg; synthesized from Example 7), same as Example 2 This operation gave the title compound (197 mg) with the following physical data. TLC: Rf 0.43 (chloroform: formazan = 17: 3); this paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 69 3 9 3 3 1 523506 A7 B7 V. Description of the invention (70) NMR ( DMSO-de): δ 9 · 89 (1H, brs), 7.93 (2H, d), 7.60 (2H, d), 7,42 (2H, d), 7.34 (2H, d) , 7.29 (lH, d), 7.06 (lH, d), 7.01 (lH, dd), 4.98 (2H, s) Fen _ Example 8 (a) -8 (p) As in Reference Examples 6, 7 and implementation The same procedures as in Examples 7 and 8 were performed to obtain the title compound having the following physical data.窨 _ _Example 8 (a) 4- (2-benzenesulfonamido-5-chlorophenoxymethyl) benzoic acid (Please read the precautions on the back before filling this page)

T L C ·· R f 0.39 (氯仿：甲醇=4:1); NMR (DMSO-d6) ： (ί 12.98 (1H, s), 9.78 (1H, s), 7.92 (2H, d), 7.65 (2H, d), 7.55 (1 H, t), 7.41 (2H, t), 7.37 (2H, d), 7.28 (1 H, d), 7.04 (1 H, dz), 6.98 (1 H, dd), 4.98 (2H, s)〇 經濟部中央標準局員工消費合作社印製 窨？fe例8 (b) 4-(2-苯磺釀胺基-4-氯苯氧甲基）苯甲酸 XOOH ,TLC ·· R f 0.39 (chloroform: methanol = 4: 1); NMR (DMSO-d6): (ί 12.98 (1H, s), 9.78 (1H, s), 7.92 (2H, d), 7.65 (2H, d), 7.55 (1 H, t), 7.41 (2H, t), 7.37 (2H, d), 7.28 (1 H, d), 7.04 (1 H, dz), 6.98 (1 H, dd), 4.98 (2H, s) 0 printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs? Example 8 (b) 4- (2-benzenesulfonylamino-4-chlorophenoxymethyl) benzoic acid XOOH,

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 7 0 3933 1 523506 A7 B7 五、發明説明（71 ) T L C : R f 0.40 (氯仿：甲醇=4 ·· 1 ); NMR (DMSO-d6) ： ^ 12.98 (1H, brs), 9.94 (1H, s), 7.90 (2H, d), 7.70 (2H, d), 7.58 (1H, t), 7.44 (2H,), 7.36 (2H, d), 7.28 (1H, d), 7.15 (1H, dd), 6.94 (1H, d), 4.97 (2H, s)〇 奮撫锎8 (c) 4-[2-(4-氯苯磺釀胺基）-4-氯苯氧甲基]苯甲酸 cr ▽ 'NH o2s ucl T L C ： R f 0.40 (氯仿··甲醇=4 : 1); NMR (DMSO-d^) ：.5 12.93 (1H, s), 10.02 (1H, s), 7.88 (2H, d), 7.61 (2H, d), 7.42 (2H, d), 7.35-7.22 (3H，m), 7.17 (1H, dd)，6.93 (1H, d), 4.94 (2H, s)。 參者例8 0-甲磺醢基 硝基-5-氣苯甲酵 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 7 0 3933 1 523506 A7 B7 V. Description of the invention (71) TLC: R f 0.40 (chloroform: methanol = 4 ·· 1); NMR (DMSO -d6): ^ 12.98 (1H, brs), 9.94 (1H, s), 7.90 (2H, d), 7.70 (2H, d), 7.58 (1H, t), 7.44 (2H,), 7.36 (2H, d), 7.28 (1H, d), 7.15 (1H, dd), 6.94 (1H, d), 4.97 (2H, s). 0 (4) 2- (2- (4-chlorobenzenesulfonate) Amine) -4-chlorophenoxymethyl] benzoic acid cr ▽ 'NH o2s ucl TLC: R f 0.40 (chloroform · methanol = 4: 1); NMR (DMSO-d ^): .5 12.93 (1H, s), 10.02 (1H, s), 7.88 (2H, d), 7.61 (2H, d), 7.42 (2H, d), 7.35-7.22 (3H, m), 7.17 (1H, dd), 6.93 (1H , d), 4.94 (2H, s). Participant Example 8 0-Methanesulfonyl nitro-5-gas benzoate (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

2-硝基-5-氯笨甲醇（400mg)之二氯申烷（6ml)溶液以 食塩-冰冷却，添加三乙胺（0.6nl)及甲基氯（0.25ml),攪 拌15分鐘。反應液中加水，Μ乙酸乙簾萃取。有機層予Μ 洗淨、乾煉及減壓湄縮，得到具下列物理數據之標題化合 物（600nig) 〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 71 39331 523506 A7 B7 經濟部中央標隼局員工消費合作社印聚 五、發明説明（72) TLC: Rf 0.36(己烷：乙酸乙酿=2:1) 參者例9 4-(2-硝基-5-氯苯基甲氧基）苯甲酸甲_A solution of 2-nitro-5-chlorobenzyl alcohol (400 mg) in dichloromethane (6 ml) was cooled with ice-ice, and triethylamine (0.6 nl) and methyl chloride (0.25 ml) were added, and stirred for 15 minutes. Water was added to the reaction solution, and the solution was extracted with ethyl acetate. The organic layer was washed, dried, and decompressed under reduced pressure to obtain the title compound (600nig) with the following physical data. ○ This paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 71 39331 523506 A7 B7 Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs V. Invention Description (72) TLC: Rf 0.36 (hexane: ethyl acetate = 2: 1) Participant Example 9 4- (2-nitro-5-chlorobenzene Methoxy) methyl benzoate_

xr COOMe 0 -甲磺醢基-2-硝基-5-氯苯甲醇（600mg;由參考例8 合成）之丙醑（lOal)溶液中，加入4-羥基苯甲酸甲酯（425 mg)及碳酸鉀（900mg),攪拌1小時。反應混合物中添加丙 酮（ΙΟιβΙ),攪拌22小時。邊瀘反應混合物，濾液減壓濃縮 。殘留物以矽膠管柱層析法（己烷-乙酸乙酯）純化，得到 具下列物理數據之標題化合物（46 3ing)。 TLC: Rf 0.26(己烷：乙酸乙酯=2:1) 參者例10 4-(2-胺基-5-氯苯基甲氧基）苯甲酸甲酯 XOOMeTo a solution of xr COOMe 0-methanesulfonyl-2-nitro-5-chlorobenzyl alcohol (600 mg; synthesized from Reference Example 8) in lOal, methyl 4-hydroxybenzoate (425 mg) and Potassium carbonate (900 mg), stirred for 1 hour. To the reaction mixture was added acetone (10 μβΙ), followed by stirring for 22 hours. The reaction mixture was stirred, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the title compound (46 3ing) with the following physical data. TLC: Rf 0.26 (hexane: ethyl acetate = 2: 1) Reference Example 10 Methyl 4- (2-amino-5-chlorophenylmethoxy) benzoate XOOMe

4-(2-硝基-5-氯苯基甲氧基）苯甲酸甲酯（460mg;由參 考例 9 合成）、T H F (1 0 π 1 )、水（3 in 1 )、 1 N 塩酸（0 · 4 ® 1 )及鐵 粉（ 500 mg)之混合物搅拌13小時。過濾反應混合物，滤液 予Μ洙淨、乾燥及減壓濃縮。殘留物以矽膠管柱曆析法（ 己烷-乙酸乙_)純化，得到具下列物理數據之標題化合物 (419mg)〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 72 3933 1 (請先閱讀背面之注意事項再填寫本頁) 523506 A7 B7 五、發明説明（73 ) TLC: Rf 0.23(己烷：乙酸乙酿=4:1) 奮_例9 4-[2-(4_氯苯磺醸胺基）-5-氯苯基甲氧基]苯甲酸甲簾Methyl 4- (2-nitro-5-chlorophenylmethoxy) benzoate (460 mg; synthesized from Reference Example 9), THF (1 0 π 1), water (3 in 1), 1 N acetic acid ( The mixture of 0 · 4 ® 1) and iron powder (500 mg) was stirred for 13 hours. The reaction mixture was filtered, and the filtrate was filtered, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (419mg) with the following physical data. This paper is in accordance with China National Standard (CNS) A4 (210X297 mm) 72 3933 1 (Please read the notes on the back before filling this page) 523506 A7 B7 V. Description of the invention (73) TLC: Rf 0.23 (hexane: ethyl acetate = 4: 1) Fen_Example 9 4- [2- ( 4-Chlorobenzenesulfonylamino) -5-chlorophenylmethoxy] benzoic acid methyl curtain

4-(2-胺基-5-氯苯基甲氧基）苯甲酸甲酯（450aig;由 參考例10合成）之二氯甲烷（4ml)溶液中，添加吡啶（0.24 ml)及4 -氯笨磺醢氯（380iag),攪拌21小時。反應液中加水 ,Μ乙酸乙酯萃取。有機層予K洗淨，乾燥並減壓濃縮。 殘留物Κ己烷-乙酸乙酯之混合溶劑再結晶而純化，得到 具下列物理數據之標題化合物（31〇ag)。 TLC : Rf 0 . 45 (笨：乙酸乙簾=9 : 1); HMR： δ8·01(2Η,ά), 7.62(2H,d), 7.40(2H,d), 7.32- 7.26(3H,m), 7-ll(lH,brs), 6*90(2H,d), 4.80(2H,s), 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 3·90 (3H · s) 奮施例1 0 4-[2-(4-氯笨磺醣胺基）-5-氯苯基甲氧基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 73 3933 1 523506 A7 B7 五、發明説明（74 )To a solution of methyl 4- (2-amino-5-chlorophenylmethoxy) benzoate (450aig; synthesized from Reference Example 10) in dichloromethane (4ml) was added pyridine (0.24 ml) and 4-chloro Bensulfonium chloride (380iag), stirred for 21 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with K, dried, and concentrated under reduced pressure. The residue was purified by recrystallization from a mixed solvent of hexane and ethyl acetate to obtain the title compound (31oag) having the following physical data. TLC: Rf 0.45 (Stupid: Ethyl acetate = 9: 1); HMR: δ8 · 01 (2Η, ά), 7.62 (2H, d), 7.40 (2H, d), 7.32- 7.26 (3H, m ), 7-ll (lH, brs), 6 * 90 (2H, d), 4.80 (2H, s), printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 3 · 90 (3H · s) Fenshi Example 1 0 4- [2- (4-chlorobenzylsulfonylamino) -5-chlorophenylmethoxy] benzoic acid The paper size applies to Chinese National Standard (CNS) A4 specifications (210X 297 mm) 73 3933 1 523506 A7 B7 V. Description of the invention (74)

使用4-[2-(4-氯苯磺酿胺基）-5-氯苯基甲氧基]苯甲 酸甲酯（300iig;由實施例9合成），如實施例2般相同操作 ,得到具下列物理數據之標題化合物（187ag)。 TLC : Rf 0 · 51 (乙酸乙 _ ); NHR (DMSO-de) ： δ 1 0 . 2 - 1 0 . 0 (1 Η ,br) , 7*90(2Hfd), 7.69 (2H,d), 7.61(2H,d), 7.49(lH,d), 7.36(lH,dd), 7·01( 1H,d) , 6·92 (2H,d)，5·02 (2H，s&gt; 參者例1 1 2-苯磺醸胺基-5-氯-1-硝基苯 — (請先閱讀背面之注意事項再填寫本頁)Using methyl 4- [2- (4-chlorobenzenesulfonylamino) -5-chlorophenylmethoxy] benzoate (300iig; synthesized from Example 9), the same operation as in Example 2 was performed to obtain The title compound (187ag) with the following physical data. TLC: Rf 0 · 51 (ethyl acetate); NHR (DMSO-de): δ 1 0. 2-1 0. 0 (1 Η, br), 7 * 90 (2Hfd), 7.69 (2H, d), 7.61 (2H, d), 7.49 (lH, d), 7.36 (lH, dd), 7.01 (1H, d), 6.92 (2H, d), 5.02 (2H, s &gt; 1 1 2-benzenesulfonamido-5-chloro-1-nitrobenzene — (Please read the notes on the back before filling this page)

、1T, 1T

經濟部中央標準局員工消費合作社印製 2-硝基-4-氯笨胺（50〇Kg)及吡啶（2.1ml)之二氯甲烷 (1 0 m 1 )溶液中，在氣氣中及0 t：下，滴加苯磺釀氯（1 . 2 ® 1 ) 。反應液於室溫攪拌3天。反應液中加氷，Μ乙酸乙酿萃 取。有機層予Μ洗淨、乾嫌及減壓濃縮。殘留物Μ乙酸乙 _ -己烷之混合溶劑使副產物再结晶。母液減壓濃縮，殘 留物Μ矽膠管柱層析法（乙酸乙酯-己烷）純化，Μ乙酸乙 酯-己烷之混合溶劑再结晶而純化，得具下列物理數據之 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐） „ λ 0 Λ 0 0 , 74 39331 523506 A7 B7 五、發明説明（75) 摞題化合物（175fflg)。 (請先閲讀背面之注意事項再填寫本頁) TLC: Rf 0.37(乙酸乙酯：己烷=1:5) 參者例12 2-苯磺醯胺基-5-氯苯胺Printed with 2-nitro-4-chlorobenzylamine (50Kg) and pyridine (2.1ml) in dichloromethane (10 m 1) solution by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs t: Next, add benzenesulfuric chloride (1.2 ® 1) dropwise. The reaction solution was stirred at room temperature for 3 days. Ice was added to the reaction solution, and M ethyl acetate was extracted. The organic layer was washed with M, dried and concentrated under reduced pressure. The residue M was a mixed solvent of ethyl acetate and hexane to recrystallize the by-product. The mother liquor was concentrated under reduced pressure, the residue was purified by silica gel column chromatography (ethyl acetate-hexane), and the mixed solvent of ethyl acetate-hexane was recrystallized and purified. National Standard (CNS) A4 specification (210X297 mm) „λ 0 Λ 0 0, 74 39331 523506 A7 B7 V. Description of the invention (75) Question title compound (175fflg). (Please read the precautions on the back before filling this page ) TLC: Rf 0.37 (ethyl acetate: hexane = 1: 5) See Example 12 2-benzenesulfonamido-5-chloroaniline

於氧氣中，2-苯磺醢胺基-5-氯-1-硝基苯（172ng;由 參考例11合成）之乙酸（4ιι1)溶液中，於室溫下添加遨原鐵 粉（154mg)。反應懸浮液在1201C搅拌2小時。反應懸浮液 以乙酸乙酯稀釋、過濾。濾液減壓濃縮，殘留物K矽膠管 柱層析法（乙酸乙_ -己烷）純化，得到具下列物理數據之 摞題化合物（92mg)。 TLC: Rf 0.34(乙酸乙酯：己烷=1:2) 奮_俐1 1 4-(2-苯磺醯胺基-5-氯苯胺基羰基）苯甲酸甲酯In oxygen, a solution of 2-benzenesulfonamido-5-chloro-1-nitrobenzene (172ng; synthesized from Reference Example 11) in acetic acid (4ι1) was added lutetium iron powder (154mg) at room temperature. . The reaction suspension was stirred at 1201 C for 2 hours. The reaction suspension was diluted with ethyl acetate and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (92 mg) having the following physical data. TLC: Rf 0.34 (ethyl acetate: hexane = 1: 2) Fen_Li1 1 4- (2-benzenesulfonamido-5-chloroanilinecarbonyl) benzoic acid methyl ester

.COOMe 經濟部中央標準局員工消費合作社印製 於氣氣流中，於含2-笨磺釀胺基-5-氯笨胺（90mg;由 參考例12合成）及吡啶（0.05ml)之二氯甲烷溶液（5ml)中， 在室溫下添加4-甲氧羰基苯甲醢氯（70ing),携拌6小時。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 75 3933 1 523506 A7 B7 五、發明説明（76 ) 反應結束後，於反應液中添加水，Μ乙酸乙_萃取。洙淨 有機層，乾燥及減壓濃縮。殘留物Κ乙酸乙酯-己烷之混 合溶劑再结晶而純化，得到具下列物理數據之標題化合物 (112fflg)〇 T L C : R f 0 . 5 5 (乙酸乙酯：己烷=1 : 1); HMR (CDC l3 + DHS0~de) ： δ 9·41 (1 Η , brs ) , 8 · 93 (1 Η , brs), 8.22(lH,d), 8‘15(2H,d), 7.98(2H,d), 7·72-7·62(2Η,ηι ),7 * 58 -7 . 45 ( 1 H , m) , 7.44-7.32(2H,ia), 6.96(lH,dd), 6 · 82 (1H , d) g _ 例 1 2 4-(2-苯磺醢胺基-5-氯苯胺羰基）苯甲酸COOMe Printed in the air stream by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, in dichloro containing 2-benzylsulfonyl-5-chlorobenzylamine (90mg; synthesized from Reference Example 12) and pyridine (0.05ml). In a methane solution (5 ml), 4-methoxycarbonylbenzidine chloride (70ing) was added at room temperature, and the mixture was stirred for 6 hours. This paper scale applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 75 3933 1 523506 A7 B7 V. Description of the invention (76) After the reaction is completed, water is added to the reaction solution, and Methyl acetate is used for extraction. The organic layer was decanted, dried and concentrated under reduced pressure. The residue K was recrystallized from a mixed solvent of ethyl acetate-hexane to obtain the title compound (112fflg) with the following physical data. TLC: R f 0.5 .5 (ethyl acetate: hexane = 1: 1); HMR (CDC l3 + DHS0 ~ de): δ 9 · 41 (1 Η, brs), 8 · 93 (1 Η, brs), 8.22 (lH, d), 8'15 (2H, d), 7.98 (2H , d), 7.72-7.62 (2Η, η), 7 * 58 -7. 45 (1 H, m), 7.44-7.32 (2H, ia), 6.96 (lH, dd), 6.82 (1H, d) g _ Example 1 2 4- (2-benzenesulfonamido-5-chloroanilinecarbonyl) benzoic acid

.COOH (請先閱讀背面之注意事項再填寫本頁).COOH (Please read the notes on the back before filling this page)

經濟部中央標準局員工消費合作社印製 使用4-(2-苯磺醯胺基-5-氯笨胺羰基）笨甲酸甲酯（ llOmg;由實施例11合成），同實施例2般操作，得到具下 列物理數據之標題化合物（107mg)。 TLC: Rf 0.36(己烷：乙酸乙簾：乙酸=1〇ί8:1); HHR(DHSO-de) ： δ 13.00(1Η,brs) , 9.80 (1 Η ,brs) , 9.65( lH,s), 8.09(2H,d), 7.87(2H,d), 7.81(lH,d), 7.65- 7.50(3H,m), 7.40(2H,t), 7.22(lH,dd), 7.14(lH,d) 參者例13 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 76 3933 1 523506 A7 B7 五、發明説明（77 ) 2-硝基-5-氯笨甲釀氯Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs using methyl 4- (2-benzenesulfonamido-5-chlorobenzylaminocarbonyl) benzate (110 mg; synthesized from Example 11), the same operation as in Example 2, The title compound (107 mg) was obtained with the following physical data. TLC: Rf 0.36 (hexane: ethyl acetate: acetic acid = 1〇ί8: 1); HHR (DHSO-de): δ 13.00 (1Η, brs), 9.80 (1Η, brs), 9.65 (lH, s) , 8.09 (2H, d), 7.87 (2H, d), 7.81 (lH, d), 7.65- 7.50 (3H, m), 7.40 (2H, t), 7.22 (lH, dd), 7.14 (lH, d ) Participant Example 13 The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 76 3933 1 523506 A7 B7 V. Description of the invention (77) 2-nitro-5-chlorobenzyl chloride

CI^^COCI ^^N02 2-硝基-5-氯苯甲酸（200mg)之磺醢氯（200βι1)溶液在 氩氣流及99 TC下攪拌4小時。冷却後，減壓濃縮，得標題 化合物。 參者锎14 1-(2-硝基-5-氯苯甲醮基）-1-(4-甲氧羰苯基）甲叉三苯磷 烷 (請先閲讀背面之注意事項再填寫本頁)CI ^^ COCI ^^ N02 A solution of 2-nitro-5-chlorobenzoic acid (200 mg) in sulfonyl chloride (200βι1) was stirred under an argon gas flow at 99 TC for 4 hours. After cooling, it was concentrated under reduced pressure to obtain the title compound. Participants: 14 1- (2-nitro-5-chlorobenzylidene) -1- (4-methoxycarbonylphenyl) methylene triphenylphosphine (Please read the precautions on the back before filling this page )

經濟部中央標準局員工消費合作社印製 4-甲氧羰基苯甲基三苯鱗溴（1.17g)之THF(8id1)溶液 中，在氩氣流下，添加第三丁醇鉀（246mg),搅拌30分鐘 。於反應液中滴加含2-硝基-5-氯苯甲釀氯（由參考例13合 成）之THFUinl)溶液，於室溫搅拌3小時。反應混合物Μ飽 和氯化銨水溶液處理，Κ氯仿萃取。有機層經洗淨、乾燥 及減壓濃縮。殘留物以矽膠管柱層析法（氯仿-甲醇）純化 ，得具下列物理數據之標題化合物（619iag)。 TLC:Rf 0.26(氯仿：甲酵=100:1) 參者例15 4-[2-(2_硝基-5-氯苯基）乙炔基]苯甲酸甲簾 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 77 3 9 33 1 523506 A7 B7 五、發明説明（78 )In the THF (8id1) solution of 4-methoxycarbonylbenzyltriphenylscale bromide (1.17g) printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, add potassium tert-butoxide (246mg) under argon flow, and stir 30 minutes. To the reaction solution was added dropwise a solution of 2-nitro-5-chlorobenzyl chloride (synthesized from Reference Example 13) in THFUinl), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was treated with a saturated aqueous ammonium chloride solution, and extracted with chloroform. The organic layer was washed, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain the title compound (619iag) having the following physical data. TLC: Rf 0.26 (chloroform: formazan = 100: 1) Participant Example 15 4- [2- (2_nitro-5-chlorophenyl) ethynyl] benzoic acid methyl curtain This paper is in accordance with Chinese national standards ( CNS) A4 specification (210X 297 mm) 77 3 9 33 1 523506 A7 B7 V. Description of the invention (78)

COOMe 含1-(2-硝基-5-氯苯甲醢基）-1-(4-甲氧羰苯基）甲叉 三笨磷烷（513mg;由參考例14合成）之鄰-三氯苯（10ml)溶 液在氩氣流及180 t：回流9小時。反應混合物予Μ減壓濃縮 ,殘留物Μ矽膠管柱層析法（己烷；乙酸乙酯）純化，得到 具下列物理數據之標題化合物（189ing)。 TLC: Rf 0.39(己烷：乙酸乙酯=7:1) 參者例1 6 4 - [2-(2-胺基-5-氛苯基）乙炔基]苯甲酸甲瞧COOMe 1- (2-nitro-5-chlorobenzylidene) -1- (4-methoxycarbonylphenyl) methanetribenzylphosphine (513 mg; synthesized from Reference Example 14) A solution of benzene (10 ml) under argon flow and 180 t: reflux for 9 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane; ethyl acetate) to give the title compound (189ing) having the following physical data. TLC: Rf 0.39 (hexane: ethyl acetate = 7: 1) Participant Example 1 6 4-[2- (2-Amino-5-aminophenyl) ethynyl] benzoic acid methyl ester

(請先閱讀背面之注意事項再填寫本頁) COOMe 經濟部中央標準局員工消費合作社印製 4-[2-(2-硝基-5-氯笨基）乙炔基]苯甲酸甲酯（180道8 由參考例15合成）之乙酸（3·6κ1)溶液中，添加邐原娥粉（ 160mg),回流30分鐘。過濾反應混合物，濾液減壓濃縮。 殘留物Μ矽膠管柱層析法（己烷-乙酸乙酷）純化，得具下 列物理數據之標題化合物（144 mg), TLC: Rf 0.25(己烷：乙酸乙酯=5:1) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 78 3933 1 523506 A7 B7 五、發明説明（79 ) 4-[2-[2-(4_氯苯磺釀胺基）-5-氯苯基]乙炔基]苯甲酸甲 酯(Please read the notes on the back before filling out this page) COOMe Printed 4- [2- (2-Nitro-5-chlorobenzyl) ethynyl] benzoic acid methyl ester (180 Lane 8 was synthesized from Reference Example 15) in an acetic acid (3.6 kappa) solution, and Sugawara E powder (160 mg) was added and refluxed for 30 minutes. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (144 mg), TLC: Rf 0.25 (hexane: ethyl acetate = 5: 1) with the following physical data The scale is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) 78 3933 1 523506 A7 B7 V. Description of the invention (79) 4- [2- [2- (4_chlorobenzenesulfonylamino) -5- Chlorophenyl] ethynyl] methyl benzoate

— (請先閱讀背面之注意事項再填寫本頁) COOMe— (Please read the notes on the back before filling this page) COOMe

4 - [2-(2-胺基-5-氯苯基）乙炔基]苯甲酸甲酿（136mg; 由參考例16合成）之二氯甲烷（2ml)溶液中，在氩氣及Ot 下，添加吡啶（77/il)及4-氯笨磺醢氛（106mg),於室溫攪 拌2 4小時。反應混合物以乙酸乙》稀釋，洗淨、乾燥及減 壓濃縮。殘留物K矽膠管柱曆析法（己烷-乙酸乙酷）純化， 得到具下列物理數據之標題化合物（ 207nig)。 TLC: Rf 0.50(己烷：乙酸乙酯=3:1) NMR: S8.07(2H,d), 7.67(2H,d), 7.58(lH,d), 7.49( 2H,d), 7·39(1Η,(1), 7.34(2H,d), 7.32(lH,dd), 7·07( 經濟部中央標準局員工消費合作社印製 1H , brs) , 3 · 96 (3H , s) 奮施例1 4 4-[2-[2-(4-氯苯磺釀胺基）-5-氯苯基]Z炔基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 79 3 93 3 1 523506 A7 B7 五、發明説明（80 )4-[2- (2-Amino-5-chlorophenyl) ethynyl] benzoic acid (136 mg; synthesized from Reference Example 16) in dichloromethane (2 ml), under argon and Ot, Add pyridine (77 / il) and 4-chlorobenzylsulfonium (106 mg), and stir at room temperature for 24 hours. The reaction mixture was diluted with ethyl acetate, washed, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain the title compound (207nig) with the following physical data. TLC: Rf 0.50 (hexane: ethyl acetate = 3: 1) NMR: S8.07 (2H, d), 7.67 (2H, d), 7.58 (lH, d), 7.49 (2H, d), 7. · 39 (1Η, (1), 7.34 (2H, d), 7.32 (lH, dd), 7.07 (printed by the Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs, 1H, brs), 3.96 (3H, s) Example 1 4 4- [2- [2- (4-Chlorobenzenesulfonylamino) -5-chlorophenyl] Z-alkynyl] benzoic acid The paper size is applicable to China National Standard (CNS) A4 (210X297) (Centi) 79 3 93 3 1 523506 A7 B7 V. Description of the invention (80)

COOHCOOH

(請先閲讀背面之注意事項再填寫本頁) 使用4-[2-[2-(4-氯苯磺醸胺基）-5-氯苯基]乙炔基] 苯甲酸甲_(1991^;由實施例13合成），如實施例2般相同 操作，得到具下列物理數據之標題化合笏（181 Bg)。 TLC: Rf 0.43(氯仿：甲酵：乙酸=100:5:1) HMR (DHSO-de) ： δ 1 3 · 1 6 (1 Η , brs) , 1 0 . 32 (1 Η , brs ), 8.00(2H,d), 7.65(2H,d), 7.59(lH,d), 7.57(2H,d), 7.50(lH,dd), 7.43(2H,d), 7.35(lH,d) 參者例1 7 4-(2-胺基-5-三氟甲基苯氧甲基）苯甲酸甲簾 COOMe 經濟部中央標準局員工消費合作社印製 NH2 使用2-硝基-5-三氟甲基酚，依參考，6 參考例12般 相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.33(己烷：乙酸乙酯=3:1) 奮_例1 5 4-(2-苯磺釀胺基-5-三氟甲基苯氧甲基）苯甲酸甲簾 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 80 3933 1 523506 A7 B7 五、發明説明（81(Please read the precautions on the back before filling this page) Use 4- [2- [2- (4-chlorobenzenesulfonylamino) -5-chlorophenyl] ethynyl] benzoic acid _ (1991 ^; Synthesized from Example 13), the same operation as in Example 2 was performed to obtain the titled chemical compound (181 Bg) with the following physical data. TLC: Rf 0.43 (chloroform: formazan: acetic acid = 100: 5: 1) HMR (DHSO-de): δ 1 3 · 1 6 (1 Η, brs), 10. 32 (1 Η, brs), 8.00 (2H, d), 7.65 (2H, d), 7.59 (lH, d), 7.57 (2H, d), 7.50 (lH, dd), 7.43 (2H, d), 7.35 (lH, d) 1 7 4- (2-Amino-5-trifluoromethylphenoxymethyl) benzoic acid methyl formaldehyde COOMe Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs NH2 Use of 2-nitro-5-trifluoromethylphenol According to the same operation as in Reference 6, Reference Example 12, the title compound with the following physical data was obtained. TLC: Rf 0.33 (hexane: ethyl acetate = 3: 1) Fen_Example 1 5 4- (2-benzenesulfonylamino-5-trifluoromethylphenoxymethyl) benzoic acid methylbenzene Paper size Applicable to China National Standard (CNS) A4 specification (210X 297 mm) 80 3933 1 523506 A7 B7 V. Description of invention (81

NH 02S COOMe F3COc 使用4-(2-胺基-5-三氟甲基苯氧基甲基）苯甲酸甲»( 由參考例17合成），依實施例7般相同操作，得到具下列物 理數據之檷題化合物。 TLC : Rf 0 . 76 (苯：丙銅=9 : 1) N M R : δ 8 · 0 5 ( 2 H , d , J = 8 ♦ 2 Η z ) , 7 · 7 7 ( 2 H , a ) , 7 · 6 9 (1 H , d , J = 8.6Hz), 7.58(lH,m), 7·45(2Η,βι), 7·25(3Η,ιη), 7·18 (lH,m), 6·99(1Η,·), 5.02(2H,s), 3.95(3H,s) 啻_锎1 fi 4-(2-苯磺釀胺基-5-三氟甲基苯氧甲基）苯甲酸 (請先閱讀背面之注意事項再填寫本頁) F3COc ,j〇rNH 02S COOMe F3COc Using 4- (2-amino-5-trifluoromethylphenoxymethyl) benzoic acid »(synthesized from Reference Example 17), the same operation as in Example 7 was performed to obtain the following physical data The title compound. TLC: Rf 0.76 (benzene: propyl copper = 9: 1) NMR: δ 8 · 0 5 (2 H, d, J = 8 ♦ 2 Η z), 7 · 7 7 (2 H, a), 7 6 9 (1 H, d, J = 8.6Hz), 7.58 (lH, m), 7.45 (2Η, βι), 7.25 (3Η, ιη), 7.18 (lH, m), 6 99 (1Η, ·), 5.02 (2H, s), 3.95 (3H, s) 啻 _ 锎 1 fi 4- (2-benzenesulfonylamino-5-trifluoromethylphenoxymethyl) benzoic acid (Please read the notes on the back before filling this page) F3COc, j〇r

C〇〇H 經濟部中央標準局員工消費合作社印製C〇〇 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

NH 02S 使用4-(2-苯磺醯胺基-5-三氟甲基苯氧甲基）苯甲酸 甲酯（由實施例15合成），依實施例2般相同操作，得到具 下列物理數據之標題化合物。 TLC: Rf 0.52(氯仿：甲醇：乙酸=100:5:1) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 81 3 93 3 1 523506 A7 B7 五、發明説明（82 ) NMR (DHSO-de) ： δ 12.95 (1 Η , brd) , 1 0 . 1 0 (1 Η , brd), 7.93(2H,d,J = 8.0Hz), 7·75(2Η,η), 7·59(1Η,πι)， 7.40-7.53(5H,a), 7.27(2H,m), 5.14(2H,s) 奮_例1 7 4-[2-(N-異丙基-苯磺釀胺基）-4-氯苯氧甲基]苯甲酸甲醮NH 02S uses methyl 4- (2-benzenesulfonamido-5-trifluoromethylphenoxymethyl) benzoate (synthesized from Example 15) and performs the same operation as in Example 2 to obtain the following physical data: Title compound. TLC: Rf 0.52 (chloroform: methanol: acetic acid = 100: 5: 1) This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) 81 3 93 3 1 523506 A7 B7 V. Description of the invention (82) NMR (DHSO-de): δ 12.95 (1 Η, brd), 1 0. 1 0 (1 Η, brd), 7.93 (2H, d, J = 8.0Hz), 7.75 (2Η, η), 7 · 59 (1Η, πι), 7.40-7.53 (5H, a), 7.27 (2H, m), 5.14 (2H, s) Fen_Example 1 7 4- [2- (N-isopropyl-benzenesulfonamide Methyl) -4-chlorophenoxymethyl] formamidine benzoate

4-(2-苯磺醢胺基-4-氯苯氧甲基）苯甲酸甲酯（402iag; 實施例7U)合成）之DMF(4ml)溶液中，添加碳酸鉀（256毫 克）及異丙基碘（185微升），室溫下攪拌一夜及在50TC搅拌 9小時。反應液中添加冰水及2N塩酸，Μ乙酸乙酯萃取。 有機層予Μ洗淨，乾燥及過滤濃縮，Μ乙醇固化後，洗淨 而得具下列物理數據之標題化合物（411mg)。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) TLC: Rf 0,59(己烷：乙酸乙酯=2:1) NMR： 8 8 · 05 (2Η , dfJ = 8 . 8Hz) , 7 . 8 3 - 7 . 79 ( 2 Η , m), 7.55-7.26(6H,m), 7*08(lH,d,J=2*8Hz), 6,89(lH,d, J=8.8Hz), 5.04(2H,s), 4.36(lH,sept,J=6.8Hz), 3.93 (3H,s), 1.05(6H,d,J=6*8Hz) 奮 _ 例 1 7 (1 ) - U ) 使用對應化合物，依參考例64參考例74實施例74 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 82 3933 1 523506 F3C、a .Ο、To a solution of 4- (2-benzenesulfonamido-4-chlorophenoxymethyl) benzoic acid methyl ester (402iag; synthesized in Example 7U)) in DMF (4ml) was added potassium carbonate (256mg) and isopropyl Base iodine (185 μl) was stirred overnight at room temperature and 9 hours at 50 TC. The reaction solution was added with ice water and 2N acetic acid, and extracted with ethyl acetate. The organic layer was washed with M, dried, filtered, and concentrated. After the M ethanol was solidified, it was washed to obtain the title compound (411 mg) having the following physical data. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) TLC: Rf 0,59 (hexane: ethyl acetate = 2: 1) NMR: 8 8 · 05 (2Η, dfJ = 8.8Hz), 7.8 3-7.79 (2 Η, m), 7.55-7.26 (6H, m), 7 * 08 (lH, d, J = 2 * 8Hz), 6,89 ( lH, d, J = 8.8Hz), 5.04 (2H, s), 4.36 (lH, sept, J = 6.8Hz), 3.93 (3H, s), 1.05 (6H, d, J = 6 * 8Hz) Fen_ Example 1 7 (1)-U) Using the corresponding compound, according to Reference Example 64 Reference Example 74 Example 74 This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 82 3933 1 523506 F3C, a.〇 ,

A7 B7 五、發明説明（83 ) 實_例17或參考例8 —參考例9·»參考例ίο —實施例9 —實 施例17相同操作，得具有下列物理數據之標題化合物。 實 Jfe 例 1 7 (1) 4-[2-(N-異丙基苯磺釀胺基卜5_三氟甲基苯氧甲基]苯甲 酸甲酯 .COOMe T L C ： R f 0.55 (己烷：乙酸乙酯= 2:1); NM R ：δ 8.07 (2H, d, J=8.4Hz), 7.79 (2H, m), 7.44-7.55 (3H, m), 7.32-7.43 (2H, m), 7.18-7.29 (3H, m), 5.10 (2H, s), 4.38 (1 H, sept, J=6.6Hz), 3.94 (3H, s), 1.05 (6H, d, J=6.6Hz)〇 奮淪锎1 7 (2) 4-[2 -（N-異丙基苯磺醢胺基）-5 -甲基苯氧甲基]苯甲酸甲 --------MWI— (請先閲讀背面之注意事項再填寫本頁) 訂 經濟部中央標準局員工消費合作社印製 酯A7 B7 V. Explanation of the Invention (83) Example 17 or Reference Example 8—Reference Example 9 · »Reference Example ο—Example 9—Example 17 The same operation was performed to obtain the title compound having the following physical data. Example Jfe Example 7 (1) 4- [2- (N-Isopropylbenzenesulfonylaminomethyl 5-trifluoromethylphenoxymethyl] benzoate methyl ester. COOMe TLC: R f 0.55 (hexane : Ethyl acetate = 2: 1); NM R: δ 8.07 (2H, d, J = 8.4Hz), 7.79 (2H, m), 7.44-7.55 (3H, m), 7.32-7.43 (2H, m) , 7.18-7.29 (3H, m), 5.10 (2H, s), 4.38 (1 H, sept, J = 6.6Hz), 3.94 (3H, s), 1.05 (6H, d, J = 6.6Hz)锎 1 7 (2) 4- [2-(N-Isopropylbenzenesulfonamido) -5 -methylphenoxymethyl] benzoic acid -------- MWI— (please first (Read the notes on the back and fill out this page) Order the printed esters of the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

COOMe 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 83 3933 1 523506 A7 B7 __ 五、發明説明（84 ) TLC ： R f 0.48 (己烷·•乙酸乙酯=2 : 1 );, (請先閱讀背面之注意事項再填寫本頁) NMR ：δ8.04 (2H, d, J=8.4Hz), 7.80 (2H, m), 7.41-7.52 (3H, m), 7.28-7.39 (2H, m), 6.97 (1H, d, J=8.6Hz), 6.73-6.80 (2H, m), 5.00 (2H, s), 4.38 (1H, sept, J=7.〇Hz), 3.93 (3H, s), 2.35 (3H, s), 1.05 (6H, d, J=7.0Hz)〇 置·例1 7 ( 3 ) 4-[2-(N-異丙基苯磺醸胺基卜5-氯苯氧甲基]苯甲酸甲酿COOMe The size of this paper applies Chinese National Standard (CNS) A4 specification (210X297 mm) 83 3933 1 523506 A7 B7 __ V. Description of the invention (84) TLC: R f 0.48 (hexane · • ethyl acetate = 2: 1) ;, (Please read the notes on the back before filling this page) NMR: δ8.04 (2H, d, J = 8.4Hz), 7.80 (2H, m), 7.41-7.52 (3H, m), 7.28-7.39 (2H, m), 6.97 (1H, d, J = 8.6Hz), 6.73-6.80 (2H, m), 5.00 (2H, s), 4.38 (1H, sept, J = 7.0 Hz), 3.93 ( 3H, s), 2.35 (3H, s), 1.05 (6H, d, J = 7.0Hz). Example 1 7 (3) 4- [2- (N-isopropylbenzenesulfonamido 5 -Chlorophenoxymethyl] benzoate

NMR ： δ 8.06 (2Η, d, J=8.2Hz), 7.78 (2H, d, J=7.2Hz), 7.25-7.48 (5H, m), 6.85-7.05 (3H, m), 5.02 (2H, s), 4.37 (1H, sept, J=6.4Hz), 3.94 (3H, s), 1.04 (6H, d, J=6.4Hz)〇 經濟部中央標準局員工消費合作社印製 奮_例17 (4丄 4-[2_(N-異丙基 基]桂皮酸甲酯 -呋喃基磺釀胺基）-5-三氟甲基苯氧甲NMR: δ 8.06 (2Η, d, J = 8.2Hz), 7.78 (2H, d, J = 7.2Hz), 7.25-7.48 (5H, m), 6.85-7.05 (3H, m), 5.02 (2H, s ), 4.37 (1H, sept, J = 6.4Hz), 3.94 (3H, s), 1.04 (6H, d, J = 6.4Hz). Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. Example 17 (4 丄4- [2_ (N-isopropyl) methyl cinnamate-furylsulfonylamino] -5-trifluoromethylphenoxymethyl

COOMe 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 84 3933 1 523506 A7 B7_ _____ 五、發明説明（85 ) TLC ： R f 0.39 (苯：乙酸乙酯=19:1); NM R ： δ 7.71 (1H, d, J=16Hz), 7.59-7.45 (5H, m), 7.23-7.20 (3H, m), 6.94-6.92 (1 H, m), 6.50-6.42 (2H, m), 5.12 (2H, s), 4.5-4.4 (1 H, m), 3.82 (3H, s), 1.09 (6H, dd, J=6.5, 2Hz)。 奮施例li 4-[2-(N-異丙基苯磺醢胺基）_4_氛苯氧甲基]苯甲酸COOMe The size of this paper applies Chinese National Standard (CNS) A4 (210X297 mm) 84 3933 1 523506 A7 B7_ _____ V. Description of the invention (85) TLC: R f 0.39 (benzene: ethyl acetate = 19: 1); NM R: δ 7.71 (1H, d, J = 16Hz), 7.59-7.45 (5H, m), 7.23-7.20 (3H, m), 6.94-6.92 (1 H, m), 6.50-6.42 (2H, m) , 5.12 (2H, s), 4.5-4.4 (1 H, m), 3.82 (3H, s), 1.09 (6H, dd, J = 6.5, 2Hz). Fenshili li 4- [2- (N-Isopropylbenzenesulfonamido) _4_ Fluphenoxymethyl] benzoic acid

使用4-[2-(N-異丙基笨磺醢胺基）-4-氯苯氧甲基]笨 甲酸甲_(實施例17合成）依實施例2之相同操作，得具下 列物理數據之標題化合物。 TLC: Rf 0.43(氯仿：甲酵：水=9:1:0.1) NMR (DMSO-de) ： δ 1 2 . 90 (1 Η , br) , 7 · 94 ( 2 Η ,d,J = 8 · 4 Ηz ), 經濟部中央標準局員工消費合作社印m (請先閱讀背面之注意事項再填寫本頁) 7.78(2H,d，J = 8.4Hz), 7·66-7·45(6Η,βι), 7.23(lH,d，J = 8·4Ηζ), 7.07(lH,d,J=2.4Hz), 5.13(2H,s), 4·20(1Η， 七峯，J = 6.6Hz), 0·99 and 0·96(各 3Η,《各 d,J = 6.6Hz) 實 l例 1 8 ( η - 1 a f 1 M ) 使用對應化合物依參考例64參考例74實施例74實 施例17 —實施例2或參考例84參考例94參考例1〇4實施 例9—實施例174實施例2之相同操作，得具下列物理數據 3933 1 85 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X297公釐）Using 4- [2- (N-isopropylbenzylsulfonamido) -4-chlorophenoxymethyl] benzylformate (synthesis of Example 17) and following the same operation as in Example 2, the following physical data were obtained Title compound. TLC: Rf 0.43 (chloroform: formazan: water = 9: 1: 0.1) NMR (DMSO-de): δ 1 2. 90 (1 Η, br), 7 · 94 (2 Η, d, J = 8 · 4 Ηz), printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 7.78 (2H, d, J = 8.4Hz), 7.66-7 · 45 (6Η, βι ), 7.23 (lH, d, J = 8 · 4Ηζ), 7.07 (lH, d, J = 2.4Hz), 5.13 (2H, s), 4.20 (1Η, seven peaks, J = 6.6Hz), 0 · 99 and 0 · 96 (each 3Η, "each d, J = 6.6Hz) Example 1 8 (η-1 af 1 M) Using the corresponding compound according to Reference Example 64 Reference Example 74 Example 74 Example 74 Example 17-Implementation Example 2 or Reference Example 84 Reference Example 94 Reference Example 104 Example 9—Example 174 The same operation as in Example 2 can be obtained with the following physical data 3933 1 85 This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 Mm)

XX 523506 A7 B7 五、發明説明（86) 之檫題化合物。 SUfe锎1 8⑴ 4-[2-(N-羧甲基苯磺醢胺基）-4-氯笨氧甲基]苯甲酸XX 523506 A7 B7 V. The title compound of the description of the invention (86). SUfe 锎 1 8⑴ 4- [2- (N-carboxymethylbenzenesulfonamido) -4-chlorobenzyloxymethyl] benzoic acid

C〇〇HC〇〇H

c丨/ 'COOH 〇2SvV^c 丨 / 'COOH 〇2SvV ^

U TLC ： R f 0.20 (氯仿：甲醇••水=7:3:0.3); NMR (DMSO-d^) :512.93 (2H, br), 7.88 (2H, d, J=8.4Hz), 7.63-7.37 (7H, m), 7.16-7.06 (3H, m), 4·88 (2H, s), 4.31 (2H，s)。 sl _ 例 18 m 4-[2-[N_(2-經乙基）苯磺醢胺基卜4-氯苯氧甲基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製U TLC: R f 0.20 (chloroform: methanol •• water = 7: 3: 0.3); NMR (DMSO-d ^): 512.93 (2H, br), 7.88 (2H, d, J = 8.4Hz), 7.63- 7.37 (7H, m), 7.16-7.06 (3H, m), 4.88 (2H, s), 4.31 (2H, s). sl _ Example 18 m 4- [2- [N_ (2-Ethyl) benzenesulfonamido 4-chlorophenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page) Ministry of Economy Printed by the Consumer Standards Cooperative of the Central Bureau of Standards

CICI

ΧΓXΓ

COOHCOOH

IT 02SIT 02S

.OH Τ L C ： R f 0.26 (氯仿：甲醇：水=9 : 1 : 0 · 1); NMR (DMS〇-d6) :δ 12.71 (1H，br)，7.88 (2H,d，J=8.4Hz)，7_63-7_32(7H,m)， 7.19-7.08 (3H, m), 4.89 (2H, brs), 4.71 (1H, br), 3.86-3.40 (4H, m)〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 86 3933 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（87 )4-[2-(N-甲基苯磺釀胺基）-4-三氟甲基苯氧甲基]苯甲酸.OH Τ LC: R f 0.26 (chloroform: methanol: water = 9: 1: 0 · 1); NMR (DMS〇-d6): δ 12.71 (1H, br), 7.88 (2H, d, J = 8.4Hz ), 7_63-7_32 (7H, m), 7.19-7.08 (3H, m), 4.89 (2H, brs), 4.71 (1H, br), 3.86-3.40 (4H, m). This paper standard applies to Chinese national standards (CNS) A4 specification (210X297 mm) 86 3933 1 523506 A7 B7 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 5. Description of the invention (87) 4- [2- (N-methylbenzenesulfonylamino)- 4-trifluoromethylphenoxymethyl] benzoic acid

C〇〇HC〇〇H

〇2S TLC ： R f 0.31 (氯仿：甲醇：水=9:1:0.1); NMR (DMSO-d6) ： δ 12.90 (1H, br), 7.90 (2H, d, J=8.4Hz), 7.76-7.70 (1H, 似 dd )，7.64-7.43 (6H，m), 7.31 (1 H, d, J=8.4Hz), 7.23 (2H, d, J=8.4Hz), 5.05 (2H, s), 3.18 (3H, s)。 實施例 1 8 (.4..)..4-[2-[N-(2-羥乙基）苯磺醣胺基]-4-三氟甲基苯氧甲基] 苯甲酸〇2S TLC: R f 0.31 (chloroform: methanol: water = 9: 1: 0.1); NMR (DMSO-d6): δ 12.90 (1H, br), 7.90 (2H, d, J = 8.4Hz), 7.76- 7.70 (1H, like dd), 7.64-7.43 (6H, m), 7.31 (1 H, d, J = 8.4Hz), 7.23 (2H, d, J = 8.4Hz), 5.05 (2H, s), 3.18 (3H, s). Example 1 8 (.4 ..) .. 4- [2- [N- (2-hydroxyethyl) benzenesulfonylamino] -4-trifluoromethylphenoxymethyl] benzoic acid

jCTjCT

C〇〇H (請先閱讀背面之注意事項再填寫本頁)C〇〇H (Please read the notes on the back before filling this page)

.OH.OH

02S T L C ： R f 0.24 (氯仿：甲醇：水=9:1:0.1); NMR (DMSO-d6) ：δ 12.51 (1H, br), 7.89 (2H, d, J=8.4Hz), 7.74 (1 H, dd, J=2.2 IL 8.4Hz), 7.62-7.37 (6H, m), 7.28 (1H, d, J=8.4Hz), 7.20 (2H, d, J=8.4Hz), 5.00 (2H, brs), 4.70 (1H, br), 3.66-3.28 (4H, m)〇 奮淪例1 8 (4-[2-[N-(2-羥乙基）苯磺醢胺基]-5-三氟甲基苯氧甲基] 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 87 3933 1 523506 A7 B7 五、發明説明（88 ) 苯甲酸 hr02S TLC: R f 0.24 (chloroform: methanol: water = 9: 1: 0.1); NMR (DMSO-d6): δ 12.51 (1H, br), 7.89 (2H, d, J = 8.4Hz), 7.74 (1 H, dd, J = 2.2 IL 8.4Hz), 7.62-7.37 (6H, m), 7.28 (1H, d, J = 8.4Hz), 7.20 (2H, d, J = 8.4Hz), 5.00 (2H, brs ), 4.70 (1H, br), 3.66-3.28 (4H, m). Example 1 8 (4- [2- [N- (2-hydroxyethyl) benzenesulfonamido] -5-trifluoro Methylphenoxymethyl] This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 87 3933 1 523506 A7 B7 V. Description of the invention (88) Benzoic acid hr

.OH 〇2s.OH 〇2s

C〇〇H τ 乙 c : R f 0.40 (氯仿：甲醇：乙酸=100:5:1); NMR (DMS〇-d6) ： δ 12.96 (1H, brd), 7.89 (2H, d, J=8.4Hz), 7.61 (2H, m), 7.34-7.58 (6H, m), 7.20 (2H, d, J=8.4Hz), 5.05 (1H, brs), 4.67 (1 H, m), 3.60 (2H, m), 3.42 (2H, m)〇 (請先閱讀背面之注意事項再填寫本頁) 衣. gLife m 1 8 f β) 訂 4-[2-(卜甲基苯磺釀胺基）-5-氯苯氧甲基]苯甲酸C〇H τ B c: R f 0.40 (chloroform: methanol: acetic acid = 100: 5: 1); NMR (DMS〇-d6): δ 12.96 (1H, brd), 7.89 (2H, d, J = 8.4 Hz), 7.61 (2H, m), 7.34-7.58 (6H, m), 7.20 (2H, d, J = 8.4Hz), 5.05 (1H, brs), 4.67 (1 H, m), 3.60 (2H, m), 3.42 (2H, m) 〇 (Please read the precautions on the back before filling out this page) Clothing. gLife m 1 8 f β) Order 4- [2- (Busylbenzenesulfonylamino) -5-chloro Phenoxymethyl] benzoic acid

經濟部中央標準局員工消費合作社印製 T L C ： R f 0.36 (氛仿：甲醇：水=9··1:0·1); NMR (DMSO-d0) ：δ 12.63 (1H, br), 7.89 (2H, d, J=8.4Hz), 7.64-7.41 (5H, m), 7.25-7.19 (4H, m)，7.05 (1H, dd, J=2.2 及 8.4Hz), 4·98 (2H, s), 3.12 (3H, s)。 謇瀹例1 8 (7) 4-[2-[执-(2-羥乙基）磺釀胺基卜5-氛苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 88 3933 1 523506 A7 B7 五、發明説明（89Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.36 (Diffuse imitation: Methanol: Water = 9 ·· 1: 0 · 1); NMR (DMSO-d0): δ 12.63 (1H, br), 7.89 ( 2H, d, J = 8.4Hz), 7.64-7.41 (5H, m), 7.25-7.19 (4H, m), 7.05 (1H, dd, J = 2.2 and 8.4Hz), 4.98 (2H, s) , 3.12 (3H, s). Example 1 8 (7) 4- [2- [Executive- (2-hydroxyethyl) sulfonylamino-5-benzylphenoxymethyl] benzoic acid This paper is sized to the Chinese National Standard (CNS) Α4 (210X 297 mm) 88 3933 1 523506 A7 B7 V. Description of the invention (89

CICI

OCOC

ITIT

.0H.0H

〇2S〇2S

COOH T L c ： R f 0.27 (氯仿：甲醇：水=9 ·· 1 : 0 · 1); NMR (DMSO-d6) ：δ 12.88 (1Η, br), 7.89 (2H, d, J=8.4Hz), 7.62-7.36 (5H, m), 7.29-7.1 7 (4H, m), 7.06 (1 H, dd, J=2.2 及 8.4Hz), 4.95 (2H, brs), 4.68 (1 H, br), 3.66-3.24 (4H, br)。 亶施锎1 8 (8)4-[2-(N-甲基苯磺醢胺基）-5-三氟甲基苯氧甲基]苯甲酸COOH TL c: R f 0.27 (chloroform: methanol: water = 9 ·· 1: 0 · 1); NMR (DMSO-d6): δ 12.88 (1Η, br), 7.89 (2H, d, J = 8.4Hz) , 7.62-7.36 (5H, m), 7.29-7.1 7 (4H, m), 7.06 (1 H, dd, J = 2.2 and 8.4Hz), 4.95 (2H, brs), 4.68 (1 H, br), 3.66-3.24 (4H, br).亶 施 锎 1 8 (8) 4- [2- (N-methylbenzenesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid

〇2SvV^^〇2SvV ^^

COOH (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.46 (氯仿：甲醇：乙酸=1〇〇:5:1); NMR ： δ 8.08 (2Η, d, J=8.0Hz), 7.68 (2H, m), 7.12-7.53 (8H, m), 4.93 (2H, s), 3.24 (3H，s)。 實施 1J _8(9)4-[2-(N-異丙基苯磺醢胺基）-5-三氟甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 89 3933 1 523506 A7 B7 五、發明説明（9〇 )COOH (Please read the notes on the back before filling this page) TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.46 (chloroform: methanol: acetic acid = 100: 5: 1); NMR: δ 8.08 ( 2Η, d, J = 8.0Hz), 7.68 (2H, m), 7.12-7.53 (8H, m), 4.93 (2H, s), 3.24 (3H, s). Implementation of 1J _8 (9) 4- [2- (N-Isopropylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid This paper is applicable to Chinese National Standard (CNS) A4 specifications ( 210X297 mm) 89 3933 1 523506 A7 B7 V. Description of the invention (90)

NMR ：δ 8.15 (2Η, d, J=8.6H2), 7.81 (2H, m), 7.52 (3H, m), 7.38 (2H, m), 7.24 (3H, m), 5·13 (2H, s)，4.40 (1H，t 峯，J=6.8Hz), 1.06 (6H, d, J=6.8Hz)。 管濂锎1 8(10) 4-[2-(N-異丙基苯磺醸胺基）-5-氯苯氧甲基]苯甲酸 (請先閲讀背面之注意事項再填寫本頁)NMR: δ 8.15 (2Η, d, J = 8.6H2), 7.81 (2H, m), 7.52 (3H, m), 7.38 (2H, m), 7.24 (3H, m), 5.13 (2H, s ), 4.40 (1H, t peak, J = 6.8Hz), 1.06 (6H, d, J = 6.8Hz). Tube 1 8 (10) 4- [2- (N-Isopropylbenzenesulfonamido) -5-chlorophenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 NM R (DMSO-d6) ：δ 12.96 (1H, br), 7.95 (2H, d, J=8.2Hz), 7.78-7.74 (2H, m), 7.65-7.43 (5H, m), 7.32 (1H, s), 7.07 (2H, s), 5.21 及 5.07 (各 1 H,各 d, J=15.6Hz)，4·21 (1H,似t 峯），0.94 (6H, d，J=6.8Hz)。 • \ y _ 例 18 (i i) 4-[2-(H-異丙基苯磺醢胺基）-4-三氟甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 90 3933 1 523506 A7 五、發明説明（91)Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (DMSO-d6): δ 12.96 (1H, br), 7.95 (2H, d, J = 8.2Hz), 7.78-7.74 (2H, m), 7.65-7.43 (5H, m), 7.32 (1H, s), 7.07 (2H, s), 5.21 and 5.07 (each 1 H, each d, J = 15.6 Hz), 4.21 (1H, like t peak), 0.94 ( 6H, d, J = 6.8Hz). • \ y _ Example 18 (ii) 4- [2- (H-Isopropylbenzenesulfonamido) -4-trifluoromethylphenoxymethyl] benzoic acid The paper size applies to Chinese National Standards (CNS) A4 specifications (210X297 mm) 90 3933 1 523506 A7 V. Description of the invention (91)

COOH T L C ： R f 0.30 (氯仿：甲醇··水=9 ·· 1 ·· 0 · 1); NMR (DMS〇-d6) :δ 13.03 (1H，br)，7·95 (2H，d，J=8.2Hz), 7.84-7.74 (3H, 7.67-7.39 (6H, m), 7·25 (1H, d, J=2.4Hz), 5.28 及 5.21 (各 1H’ 各 d， J=16.6Hz)，4.26 (1H，似七峯），〇·98 及 0.97 (各 3H，各 d，J=6.6Hz)。 奮敝例18 (12) 4-[2-[H-(2-甲氧乙氧甲基）苯磺醢胺基]-4-氛苯氧甲基] 苯甲酸COOH TLC: R f 0.30 (chloroform: methanol · · water = 9 ·· 1 ·· 0 · 1); NMR (DMS〇-d6): δ 13.03 (1H, br), 7.95 (2H, d, J = 8.2Hz), 7.84-7.74 (3H, 7.67-7.39 (6H, m), 7.25 (1H, d, J = 2.4Hz), 5.28 and 5.21 (1H 'each d, J = 16.6Hz), 4.26 (1H, like seven peaks), 0.98 and 0.97 (each 3H, each d, J = 6.6Hz). Example 18 (12) 4- [2- [H- (2-methoxyethoxymethyl) Phenyl) sulfenylamino] -4-phenphenoxymethyl] benzoic acid

COOHCOOH

CI n， cr 〇2s、 .OMe Ό 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.40 (氯仿：甲醇：水= 9:1:0.1); NMR (DMSO-d6) ：δ 12.98 (1H, br), 7.91 (2H, d, J=8.2Hz), 7.66-7.52 (3H, m), 7.45-7.38 (3H, m), 7.26-7.22 (3H, m), 7.10 (1H, d, J=8.2Hz), 5.06 (2H, brs),4·92 (2H, brs)，3.68-3.63 (2H,似 t), 3.42-3.37 (2H,似 t ), 3.21 (3H，s)。 奮淪例1 83) 4 - [2-[N-(2-甲氧乙基）笨磺醢胺基]-4-氯苯氧甲基]笨甲 酸 C请先閱讀背面之注意事項存填寫本頁)CI n, cr 〇2s, .OMe TL TLC printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.40 (chloroform: methanol: water = 9: 1: 0.1); NMR (DMSO-d6): δ 12.98 (1H , br), 7.91 (2H, d, J = 8.2Hz), 7.66-7.52 (3H, m), 7.45-7.38 (3H, m), 7.26-7.22 (3H, m), 7.10 (1H, d, J = 8.2Hz), 5.06 (2H, brs), 4.92 (2H, brs), 3.68-3.63 (2H, like t), 3.42-3.37 (2H, like t), 3.21 (3H, s). Example 1 83) 4-[2- [N- (2-methoxyethyl) benzylsulfonamido] -4-chlorophenoxymethyl] benzylcarboxylic acid C, please read the precautions on the back and fill in this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 91 3 93 3 1 523506 A7 B7 五、發明説明（92)This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 91 3 93 3 1 523506 A7 B7 V. Description of the invention (92)

C〇〇HC〇〇H

CICI

/0C OMe/ 0C OMe

02S T L C : R f 0.25 (氯仿：甲醇：水=9 : 1 : 0.· 1); NMR (DMS〇-d0) :δ 12.92 (1H，br), 7.88 (2H,d，J=8.2Hz), 7.64-7.39 (6H, m), 7.22-7.10 (4H, m), 4.91 (2H, brs), 3.69 (2H, br), 3.38-3.33 (2H, m), 3.13 (3H, s)〇 奮）fe 例 18 (14)4-[2-[N-[2-(2-甲氧乙氧基）乙基]苯磺醢胺基]-4-氯苯氧 甲基]苯甲酸02S TLC: R f 0.25 (chloroform: methanol: water = 9: 1: 0. · 1); NMR (DMS〇-d0): δ 12.92 (1H, br), 7.88 (2H, d, J = 8.2Hz) , 7.64-7.39 (6H, m), 7.22-7.10 (4H, m), 4.91 (2H, brs), 3.69 (2H, br), 3.38-3.33 (2H, m), 3.13 (3H, s) ) Fe Example 18 (14) 4- [2- [N- [2- (2-methoxyethoxy) ethyl] benzenesulfonamido] -4-chlorophenoxymethyl] benzoic acid

OMeOMe

COOH (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印裝 丁 L C : R f 0.29 (氯仿··甲醇：水= 9:1:0.1); NMR (DMSO-d6) ：δ 12.95 (1Η, br), 7.89 (2H, d, J=8.2Hz), 7.65-7.39 (6H, m), 7.25 (1 H, d, ϋ=2.6Ηζ), 7.20 (2H, d, J=8.2Hz), 7.11 (1 H, d, J=8.2Hz), 4.92 (2H, brs), 3.69 (2H，br), 3.47-3.28 (6H, m)，3.19 (3H, s)。 g _ 锎 1 8 (1 5丄4-[2-(N-乙基苯磺醣胺基）-4-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 92 3933 1 523506 A7 B7 五、發明説明（93COOH (Please read the notes on the back before filling out this page) Printed Ding LC: R f 0.29 (Chloroform ·· Methanol: Water = 9: 1: 0.1); NMR (DMSO-d6) ): Δ 12.95 (1Η, br), 7.89 (2H, d, J = 8.2Hz), 7.65-7.39 (6H, m), 7.25 (1 H, d, ϋ = 2.6Ηζ), 7.20 (2H, d, J = 8.2Hz), 7.11 (1 H, d, J = 8.2Hz), 4.92 (2H, brs), 3.69 (2H, br), 3.47-3.28 (6H, m), 3.19 (3H, s). g _ 锎 1 8 (1 5 丄 4- [2- (N-ethylbenzenesulfonylamino) -4-chlorophenoxymethyl] benzoic acid The paper size applies to Chinese National Standard (CNS) A4 specification (210X297 Mm) 92 3933 1 523506 A7 B7 V. Description of the invention (93

C〇〇HC〇〇H

TLC ： R f 0.51 (氯仿：甲醇= 9:1); NM R ： δ 8.08 (2Η, d, J=8.2Hz), 7.8-7.6 (2H, m), 7.5-7.2 (7H, m), 6.81 J=9.4Hz), 4.88 (2H, s), 3.67 (2H, q, J=7.0Hz), 1.11 (3H, t, J=7.0Hz)〇 奮 _ 俐 1 8 f 1 fi) 4-[2-(N-丙基苯磺醯胺基）-4-氯苯氧甲基]苯甲酸 H,d, (請先閱讀背面之注意事項再填寫本頁)TLC: R f 0.51 (chloroform: methanol = 9: 1); NM R: δ 8.08 (2Η, d, J = 8.2Hz), 7.8-7.6 (2H, m), 7.5-7.2 (7H, m), 6.81 J = 9.4Hz), 4.88 (2H, s), 3.67 (2H, q, J = 7.0Hz), 1.11 (3H, t, J = 7.0Hz) 〇 Fen_ Li 1 8 f 1 fi) 4- (2 -(N-propylbenzenesulfonamido) -4-chlorophenoxymethyl] benzoic acid H, d, (Please read the precautions on the back before filling this page)

Cl /〇cCl / 〇c

-XT 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.50 (氯仿：甲醇=9:1); NM R ： δ 8.08 (2H, d, J=8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 6.80 (1 H, d, J=9.6Hz)， 4.85 (2H, s), 3.6-3.5 (2H, m), 1.6-1.4 (2H, m), 0.89 (3H, t, J=7.2Hz)〇 管施例18 M 7、 ' 4-[2-(卜丁基苯磺釀胺基）-4-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 93 39331 523506 A7 B7-XT Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.50 (chloroform: methanol = 9: 1); NM R: δ 8.08 (2H, d, J = 8.4Hz), 7.7-7.6 (2H, m ), 7.5-7.2 (7H, m), 6.80 (1 H, d, J = 9.6Hz), 4.85 (2H, s), 3.6-3.5 (2H, m), 1.6-1.4 (2H, m), 0.89 (3H, t, J = 7.2Hz) Tube Example 18 M 7, '4- [2- (Bubutylbenzenesulfonylamino) -4-chlorophenoxymethyl] benzoic acid The paper size applies to Chinese national standards (CNS) A4 size (210X 297 mm) 93 39331 523506 A7 B7

經濟部中央標隼局員工消費合作社印t 五、發明説明（94 )Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs V. Description of Invention (94)

XTXT

C〇〇HC〇〇H

CICI

02S TL C ： R f 0.53 (氯仿：甲醇= 9:1); NM R ： δ 8.08 (2H, d, J=8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 6.80 (1 H, d, J=9.4Hz), 4.86 (2H, s), 3.7-3.5 (2H, m), 1.5-1.2 (4H, m), 0.85 (3H, t, J=7.0Hz)〇 置施例18 ( l&amp;JL4 - [2-(N-戊基苯磺醢胺基）-4-氯苯氧甲基]苯甲酸02S TL C: R f 0.53 (chloroform: methanol = 9: 1); NM R: δ 8.08 (2H, d, J = 8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m) , 6.80 (1 H, d, J = 9.4Hz), 4.86 (2H, s), 3.7-3.5 (2H, m), 1.5-1.2 (4H, m), 0.85 (3H, t, J = 7.0Hz) 〇 Example 18 (l &amp; JL4-[2- (N-pentylbenzenesulfonamido) -4-chlorophenoxymethyl] benzoic acid

T L C ： R f 0.56 (氯仿：甲醇=9 : 1) ·， NM R ： δ 8.08 (2H, d, J=8.2Hz), 77-7.6 (2H, m), 7.5-7.2 (7H, m), 6.8-6.7 (1H, m), 4.86 (2H,s), 3.6-3.5 (2H, m), 1.5-1.2 (6H, m), 0.9-0.8 (3H, m)〇奮淪例1 8 (、4-[2-(N-己基苯磺醢胺基）-4-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） (請先閱讀背面之注意事項再填寫本頁) 523506 A7 B7 五、發明説明（95TLC: R f 0.56 (chloroform: methanol = 9: 1) ·, NM R: δ 8.08 (2H, d, J = 8.2Hz), 77-7.6 (2H, m), 7.5-7.2 (7H, m), 6.8-6.7 (1H, m), 4.86 (2H, s), 3.6-3.5 (2H, m), 1.5-1.2 (6H, m), 0.9-0.8 (3H, m). Example 1 8 (, 4- [2- (N-hexylbenzenesulfonamido) -4-chlorophenoxymethyl] benzoic acid The paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) (Please read the note on the back first Please fill in this page for matters) 523506 A7 B7 V. Description of Invention (95

C〇〇HC〇〇H

T L C ： R f 0.58 (氯仿：甲醇=9:1); NM R ： δ 8.08 (2H, d, J=8.6Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 6.9-6.8 (1 H, m), 4.86 (2H, s), 3.6-3.5 (2H, m), 1.5-1.1 (8H, m), 0.9-0.8 (3H, m)〇 奮施例1 8 (20) 4-[2-(N-苄基苯磺釀胺基）-4-氯苯氧甲基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)TLC: R f 0.58 (chloroform: methanol = 9: 1); NM R: δ 8.08 (2H, d, J = 8.6Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 6.9 -6.8 (1 H, m), 4.86 (2H, s), 3.6-3.5 (2H, m), 1.5-1.1 (8H, m), 0.9-0.8 (3H, m). Example 1 8 (20 ) 4- [2- (N-Benzylbenzenesulfonylamino) -4-chlorophenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 T L C ： R f 0.60 (氯仿：甲醇= 9:1); NM R ： δ 8.09 (2Η, d, J=8.6Hz), 7.8-7.7 (2H, m), 7.6-7.3 (3H, m), 7.3-7.1 (9H, m), 6.71 (1H, d, J=8.8Hz), 4.82 (2H, s), 4.78 (2H, s)。 實施例1 8 ( 2 1) 4-[2-(卜異丙基苯磺醢胺基）-5 -甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（21 OX 297公釐） 95 3933 1 iTLC printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.60 (chloroform: methanol = 9: 1); NM R: δ 8.09 (2Η, d, J = 8.6Hz), 7.8-7.7 (2H, m), 7.6-7.3 (3H, m), 7.3-7.1 (9H, m), 6.71 (1H, d, J = 8.8Hz), 4.82 (2H, s), 4.78 (2H, s). Example 1 8 (2 1) 4- [2- (Isopropylbenzenesulfonamido) -5 -methylphenoxymethyl] benzoic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specification (21 OX 297 mm) 95 3933 1 i

02S 523506 A7 B7 五、發明説明（9602S 523506 A7 B7 V. Description of the invention (96

COOH TLC ： R f 0.50 (氯仿：甲醇：乙酸=1 0 0 : 5 : 1); NMR ：δ 8.13 (2Η, d, J=8.2Hz), 7.82 (2H, m), 7.49 (3H, m), 7.36 (2H, m), 6.98 (1H, d, J=8.6Hz), 6.77 (2H, m), 5.05 (2H, s), 4.40 (1H，t 峯，j=6_6Hz), 2·36 (3H, s), 1.05 (6H，d, J=6.6Hz)。 簠施例1 8 ( 2 2 ) 4-[2-(N-甲基苯磺醢胺基）-5-甲基苯氧甲基]苯甲酸COOH TLC: R f 0.50 (chloroform: methanol: acetic acid = 1 0 0: 5: 1); NMR: δ 8.13 (2Η, d, J = 8.2Hz), 7.82 (2H, m), 7.49 (3H, m) , 7.36 (2H, m), 6.98 (1H, d, J = 8.6Hz), 6.77 (2H, m), 5.05 (2H, s), 4.40 (1H, t peak, j = 6_6Hz), 2.36 ( 3H, s), 1.05 (6H, d, J = 6.6Hz). Example 1 8 (2 2) 4- [2- (N-methylbenzenesulfonamido) -5-methylphenoxymethyl] benzoic acid

COOH --------— (請先閲讀背面之注意事項再填寫本頁) 訂COOH --------— (Please read the notes on the back before filling this page) Order

MeMe

__. T L C ： R f 0.56 (乙酸乙酯：己烷：乙酸=9:10:1); 經濟部中央標準局員工消費合作社印t NMR (DMSO-d6) ：δ 12.96 (1Η, brs), 7.89 (2H, d, J=8.5Hz), 7.67-7.40 (5H, m), 7.23 (2H, d, J=8.0Hz), 7.06 (1H, d, J=8.0Hz), 6.93 (1H, s), 6.78 (1H, d, J=8.0Hz), 4.93 (2H, s), 3.12 (3H, s), 2.30 (3H, s)〇 g施例18 (2m 4-[2-[N-(2-羥乙基）苯磺醣胺基]-5-甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 96 3933 1 523506 A7 B7 五、發明説明（97 )__. TLC: R f 0.56 (ethyl acetate: hexane: acetic acid = 9: 10: 1); t NMR (DMSO-d6): δ 12.96 (1Η, brs), 7.89 (2H, d, J = 8.5Hz), 7.67-7.40 (5H, m), 7.23 (2H, d, J = 8.0Hz), 7.06 (1H, d, J = 8.0Hz), 6.93 (1H, s) , 6.78 (1H, d, J = 8.0Hz), 4.93 (2H, s), 3.12 (3H, s), 2.30 (3H, s) 0 g Example 18 (2m 4- [2- [N- (2 -Hydroxyethyl) benzenesulfonylamino] -5-methylphenoxymethyl] benzoic acid The paper size applies to the Chinese National Standard (CNS) A4 (210X297 mm) 96 3933 1 523506 A7 B7 V. Description of the invention (97)

T L C ： R f 0.27 (乙酸乙酯：己烷··乙酸=9 ·· 1 〇 ♦· 1); NMR (DMSO-d6) ：δ 12.95 (1H, brs), 7.87 (2H, d, J=8.5Hz), 7.55-7.32 (5H, m), 7.20 (2H, d, J=8.5Hz), 7.08 (1H, d, J=8.0Hz), 6.91 (1H, s), 6.77 (1H, d, J=8.0Hz), 4.89 (2H, brs), 4.63 (1H, t, J=4.0Hz), 3.50-3.20 (4H, m), 2.29 (3H, s)〇 宣 _ 例 18 (24) 4-[2-[H-(丙-2-烯基）苯磺醢胺基卜4-氯苯氧甲基]苯甲酸TLC: R f 0.27 (ethyl acetate: hexane · acetic acid = 9 · 1 〇 1 · 1); NMR (DMSO-d6): δ 12.95 (1H, brs), 7.87 (2H, d, J = 8.5 Hz), 7.55-7.32 (5H, m), 7.20 (2H, d, J = 8.5Hz), 7.08 (1H, d, J = 8.0Hz), 6.91 (1H, s), 6.77 (1H, d, J = 8.0Hz), 4.89 (2H, brs), 4.63 (1H, t, J = 4.0Hz), 3.50-3.20 (4H, m), 2.29 (3H, s). Example 18 (24) 4- [ 2- [H- (prop-2-enyl) benzenesulfonamido 4-chlorophenoxymethyl] benzoic acid

(請先閱讀背面之注意事項再填寫本頁) 、1' 經濟部中央標準局目〈工消費合作社印裝 T L C ： R f 0.54 (氯仿：甲醇=9 : 1 ); NM R ： δ 8.08 (2Η, d, J=8.0Hz), 7.8-7.6 (2H, m), 7.6-7.2 (7H, m), 6.78 (1 H, d, J=9.4Hz), 5.9-5.6 (1H, m), 5.2-5.0 (2H, m), 4.86 (2H, s), 4.3-4.2 (2H, m)〇 啻 _ 例 1 8 (2 4-[2-(H-環戊基苯磺醯胺基）-4-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 97 3933 1 523506 A7 B7 五、發明説明（98(Please read the precautions on the back before filling out this page), 1 'The Central Standards Bureau of the Ministry of Economic Affairs <Printing TLC of Industrial and Consumer Cooperatives: R f 0.54 (chloroform: methanol = 9: 1); NM R: δ 8.08 (2Η , d, J = 8.0Hz), 7.8-7.6 (2H, m), 7.6-7.2 (7H, m), 6.78 (1 H, d, J = 9.4Hz), 5.9-5.6 (1H, m), 5.2 -5.0 (2H, m), 4.86 (2H, s), 4.3-4.2 (2H, m) 〇 啻 _ Example 1 8 (2 4- [2- (H-cyclopentylbenzenesulfonamido) -4 -Chlorophenoxy] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 97 3933 1 523506 A7 B7 V. Description of the invention (98

COOH T L C ： R f 0.47 (氯仿··甲醇=9 : 1); NM R ：δ8.13 (2H, d, J=8.4Hz), 7.9-7.8 (2H, m), 7.6-7.2 (6H, m), 7.07 (1 H, d, J=2.6Hz), 6.88 (1H, d, J=8.8Hz), 5.1-5.0 (2H, m), 4.5-4.3 (1 H, m)，2.0-1.7 (2H，m)，1.6-1.2 (6H，m)。 奮）fe 锎 1 8 (26) 4-[2-[N-(2 -甲氧乙基）苯磺酿胺基]-5-三氟甲基苯氧甲基 ]苯甲酸COOH TLC: R f 0.47 (chloroform · methanol = 9: 1); NM R: δ8.13 (2H, d, J = 8.4Hz), 7.9-7.8 (2H, m), 7.6-7.2 (6H, m ), 7.07 (1 H, d, J = 2.6Hz), 6.88 (1H, d, J = 8.8Hz), 5.1-5.0 (2H, m), 4.5-4.3 (1 H, m), 2.0-1.7 ( 2H, m), 1.6-1.2 (6H, m). Fen) fe 锎 1 8 (26) 4- [2- [N- (2-methoxyethyl) benzenesulfonylamino] -5-trifluoromethylphenoxymethyl] benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

.OMe 經 濟 部 中 標 準 工 消 費 合 作 社 印 製 TLC : Rf 0.46 (氯仿：甲醇♦·乙酸=1〇0:5:1); NMR ：δ 8.07 (2Η, d, J=8.4Hz), 7.66 (2H, m), 7.18-7.53 (7H, m), 7.12 (1H, m), 4.90 (2H, s), 3.81 (2H, m), 3.51 (2H, t, J=6.0Hz), 3.24 (3H, s)。 啻施例1 8 f ?· 7 ) 4-[2-(N-乙基苯磺醢胺基）-5-三氟甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 98 3933 1 523506 A7 B7 五、發明説明（99.OMe TLC printed by Standard Industrial Consumer Cooperatives: Rf 0.46 (chloroform: methanol ♦ · acetic acid = 1OO: 5: 1); NMR: δ 8.07 (2Η, d, J = 8.4Hz), 7.66 (2H , m), 7.18-7.53 (7H, m), 7.12 (1H, m), 4.90 (2H, s), 3.81 (2H, m), 3.51 (2H, t, J = 6.0Hz), 3.24 (3H, s). Example 1 8 f? 7) 4- [2- (N-Ethylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specifications (210X297 mm) 98 3933 1 523506 A7 B7 V. Description of the invention (99

XX N〆XX N〆

〇2S〇2S

C〇〇HC〇〇H

T L C ： R f 0.43 (氯仿：甲醇=9:1); NM R ： δ 8.09 (2H, d, J=8.4Hz), 77-7.6 (2H, m), 7.5-7.2 (7H, m), 7.15 (1 H, d, J=1.6Hz), 4.94 (2H, s), 3.69 (2H, q, J=7.4Hz), 1.11 (3H, t, J=7.4Hz)〇 實L施例1 8 ( 2 8 )4-[2-(H-丙基苯磺醢胺基）-5-三氟甲基笨氧甲基]苯甲酸 XOOHTLC: R f 0.43 (chloroform: methanol = 9: 1); NM R: δ 8.09 (2H, d, J = 8.4Hz), 77-7.6 (2H, m), 7.5-7.2 (7H, m), 7.15 (1 H, d, J = 1.6Hz), 4.94 (2H, s), 3.69 (2H, q, J = 7.4Hz), 1.11 (3H, t, J = 7.4Hz). Example 1 8 ( 2 8) 4- [2- (H-propylbenzenesulfonamido) -5-trifluoromethylbenzyloxymethyl] benzoate XOOH

--------嫌衣-- (請先閱讀背面之注意事項再填寫本頁) 訂 ___ 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.5 (氯仿：甲醇=9 : 1); NM R ： δ 8.09 (2Η, d, J=8.2Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 7.14 (1 H, s), 4.92 (2H, s), 3.59 (2H, t, J=7.4Hz), 1.6-1.4 (2H, m), 0.88 (3H, t, J=7.4Hz)〇 窨 _ 例 1 8 4-[2-(N-異丁基苯磺醢胺基）-5-三氟甲基苯氧甲基]笨甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 9 9 3933 1 523506 A7 B7 五、發明説明（l〇3-------- Suspect-(Please read the precautions on the back before filling this page) Order ___ Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.5 (chloroform: methanol = 9: 1); NM R: δ 8.09 (2Η, d, J = 8.2Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 7.14 (1 H, s), 4.92 (2H, s ), 3.59 (2H, t, J = 7.4Hz), 1.6-1.4 (2H, m), 0.88 (3H, t, J = 7.4Hz) 〇 窨 _ Example 1 8 4- [2- (N-isobutyl Benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] stearic acid The paper size is applicable to the Chinese National Standard (CNS) A4 (210X297 mm) 9 9 3933 1 523506 A7 B7 V. Description of the invention ( l〇3

C〇〇H f3c T L C ： R f 0.53 (氯仿：甲醇= 9:1); NM R ： δ 8.10 (2H, d, J=8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 7.11 (1 H, d, J=1.6Hz), 5.0-4.8 (2H, m), 3.44 (2H, d, J=7.4Hz), 1.7-1.5 (1 H, m), 0.90 (6H, d, J=6.4Hz)〇 簠例 i « (3(n l[2-(N-環戊基苯磺醢胺基）-5-三氟甲基苯氧甲基]苯甲 酸C〇H f3c TLC: R f 0.53 (chloroform: methanol = 9: 1); NM R: δ 8.10 (2H, d, J = 8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H , m), 7.11 (1 H, d, J = 1.6Hz), 5.0-4.8 (2H, m), 3.44 (2H, d, J = 7.4Hz), 1.7-1.5 (1 H, m), 0.90 ( 6H, d, J = 6.4Hz). Example i «(3 (nl [2- (N-cyclopentylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid

02S02S

COOH 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 丁 L C : R f 〇·54 (氛仿··甲醇=9:1); NM R ： δ 8.15 (2Η, d, J=8.0Hz), 7.8-7.7 (2H, m), 7.6-7.3 (5H, m), 7.3-7.2 (3H, m), 5.2-5.0 (2H, m), 4.5-4.3 (1H, m), 2.0-1.8 (2H, m), 1.6-1.2 (6H, m)〇 g mm i8(3n 4-[2-(N-(丙-2-烯基）笨磺醸胺基]-5-三氟甲基苯氧甲基] 苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 100 39 33 1 523506 A7 B7 五、發明説明（101)Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs of COOH (please read the precautions on the back before filling this page) Ding LC: R f 〇 · 54 (Fluent ·· Methanol = 9: 1); NM R ： δ 8.15 ( 2Η, d, J = 8.0Hz), 7.8-7.7 (2H, m), 7.6-7.3 (5H, m), 7.3-7.2 (3H, m), 5.2-5.0 (2H, m), 4.5-4.3 ( 1H, m), 2.0-1.8 (2H, m), 1.6-1.2 (6H, m) 0g mm i8 (3n 4- [2- (N- (prop-2-enyl) benzylsulfonamido] -5-Trifluoromethylphenoxymethyl] Benzoic acid The paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 100 39 33 1 523506 A7 B7 V. Description of the invention (101)

N j〇rN j〇r

COOH TLC ： R f 0.47 (氛仿：甲醇=9 : 1); NMR ： δ 8.10 (2H, d, J=8.6Hz), 7.8-7.6 (2H, m), 7.6-7.2 (7H, m), 7.12 (1H, s), 5.9-5.6 (1H, m), 5.1-5.0 (2H, m), 4.93 (2H, s), 4.24 (2H, d，J=6.2Hz)。 g 施例 18 (32) 4-[2-[N-(2 -甲基丙-2-烯基）苯磺釀胺基]-5-三氟甲基苯 氧甲基]苯甲酸COOH TLC: R f 0.47 (methanol: 9 = 1); NMR: δ 8.10 (2H, d, J = 8.6Hz), 7.8-7.6 (2H, m), 7.6-7.2 (7H, m), 7.12 (1H, s), 5.9-5.6 (1H, m), 5.1-5.0 (2H, m), 4.93 (2H, s), 4.24 (2H, d, J = 6.2Hz). g Example 18 (32) 4- [2- [N- (2-methylprop-2-enyl) benzenesulfonylamino] -5-trifluoromethylphenoxymethyl] benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 T L C : R f 〇.48 (氛仿：甲酵=9 ·· 1 ); NMR ： 5 8.10 (2H, d, J=8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 7.10 (1H, s), 4.89 (2H, s), 4·71 (2H, d, J=12_0Hz), 4.20 (2H, s), 1.74 (3H, s)。 奮施例1 8 ( 3 3 ) ' 4-[2-(N-異丙基-4 -甲基苯磺醢胺基）-5-三氟甲基苯氧甲 基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 101 3933 1 523506 A7 B7COOH (Please read the notes on the back before filling this page) TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 〇.48 (Diffuse: Formazan = 9 ·· 1); NMR: 5 8.10 (2H , d, J = 8.4Hz), 7.7-7.6 (2H, m), 7.5-7.2 (7H, m), 7.10 (1H, s), 4.89 (2H, s), 4.71 (2H, d, J = 12_0Hz), 4.20 (2H, s), 1.74 (3H, s). Example 1 8 (3 3) '4- [2- (N-Isopropyl-4 -methylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid Applicable to paper size China National Standard (CNS) A4 specification (210X 297 mm) 101 3933 1 523506 A7 B7

五、發明説明（1 02)V. Description of Invention (1 02)

COOHCOOH

T L C ： R f 0.60 (氯仿：甲醇：乙酸= ι〇〇:5:1); NM R ： δ 8.1 4 (2Η, d, J=8.4Hz), 7.68 (2H, d, J=8.2Hz), 7.52 (2H, d, J=8.2Hz), 7.19 (5H，m,芳族），5.I4 (2H，s), 4.38 (1H,七峯，J=6.8Hz)，2.38 (3H, s), 1.05 (6H, d, J=6.8Hz)〇 奮 _ 锎 1 8 () 4-[2-(N-異丙基-4-氟苯磺醢胺基）-5-三氟甲基苯氧甲基] 笨甲酸TLC: R f 0.60 (chloroform: methanol: acetic acid = ι〇〇: 5: 1); NM R: δ 8.1 4 (2Η, d, J = 8.4Hz), 7.68 (2H, d, J = 8.2Hz), 7.52 (2H, d, J = 8.2Hz), 7.19 (5H, m, aromatic), 5.I4 (2H, s), 4.38 (1H, seven peaks, J = 6.8Hz), 2.38 (3H, s) , 1.05 (6H, d, J = 6.8Hz) 〇fen_ 锎 1 8 () 4- [2- (N-isopropyl-4-fluorobenzenesulfonamido) -5-trifluoromethylphenoxy Methyl] stearic acid

八 XOOH (請先閲讀背面之注意事項再填寫本頁)Eight XOOH (Please read the notes on the back before filling this page)

〇 NIS F3C〇 NIS F3C

經濟部中央標準局員工消費合作社印$L T L C : R f 0.60 (氮仿：甲醇：乙酸=1 0 〇 ·· 5 ·· 1 ); ΝΜ R :δ 8.16 (2Η，d，J=8.2Hz)，7.76 (2Η，m，芳族），7.52 (2Η，d，J=8.2Hz)，7.26 (3H，m，芳族），7.〇1 (2H, m，芳族），5.10 (2H，dd，J=1L8, 14.6Hz)，4·38 〇Η, 七峯，J=6.4Hz)，1.09 (3H，d, J=6.4Hz), 1 ·07 (3H, d J=6.4l4z)。 管淪例1 8 ΡΠ 4-[2-(H-異丙基-4 -甲氧基苯磺釀胺基卜5-三氟甲基苯氧 甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨〇X297公釐） 102 393 3 1 523506 A7 B7 五、發明説明（103)Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: $ LTLC: R f 0.60 (nitroform: methanol: acetic acid = 1 0 〇 · 5 ·· 1); NM R: δ 8.16 (2Η, d, J = 8.2Hz), 7.76 (2Η, m, aromatic), 7.52 (2Η, d, J = 8.2Hz), 7.26 (3H, m, aromatic), 7.01 (2H, m, aromatic), 5.10 (2H, dd , J = 1L8, 14.6Hz), 4.38 〇Η, seven peaks, J = 6.4Hz), 1.09 (3H, d, J = 6.4Hz), 1.07 (3H, d J = 6.4l4z). Example 1 8 ΡΠ 4- [2- (H-Isopropyl-4 -methoxybenzenesulfonylaminotrifluorobutane 5-trifluoromethylphenoxymethyl] benzoic acid This paper is in accordance with Chinese national standards ( CNS) A4 specification (2 丨 〇297mm) 102 393 3 1 523506 A7 B7 V. Description of the invention (103)

八 XOOHEight XOOH

T L C ： R f 0.60 (氯仿：甲醇：乙酸=100:5:1); NMR ： 5 8.15 (2H, d, J=8.2Hz), 772 (2H,d, J=8.8Hz), 7.53 (2H, d, J=8.2Hz), 7.18 (3H, m，芳族），6.81 (2H, d，J=9.2Hz), 5.14 (2H，s), 4_35 (1H,七峯， J=6.4Hz)，3.83 (3H，s)，1.08 (3H，d，J=6.4Hz)，1.05 (3H，d，J=6.4Hz)。 啻）fe 俐 1 8 M ft ) 4-[2-(N-異丙基苯确醢胺基）-5-氯苯氧甲基]苯甲酸TLC: R f 0.60 (chloroform: methanol: acetic acid = 100: 5: 1); NMR: 5 8.15 (2H, d, J = 8.2Hz), 772 (2H, d, J = 8.8Hz), 7.53 (2H, d, J = 8.2Hz), 7.18 (3H, m, aromatic), 6.81 (2H, d, J = 9.2Hz), 5.14 (2H, s), 4_35 (1H, seven peaks, J = 6.4Hz), 3.83 (3H, s), 1.08 (3H, d, J = 6.4Hz), 1.05 (3H, d, J = 6.4Hz).啻) Fei 1 8 M ft) 4- [2- (N-Isopropylbenzylamino) -5-chlorophenoxymethyl] benzoic acid

八 /COOH (請先閱讀背面之注意事項再填寫本頁)Eight / COOH (Please read the notes on the back before filling out this page)

經濟部中央標準局員工消費合作社印製 T L C ： R f 0.36 (氮仿：甲醇= 9:1); NM R ： 5 8.11 (2H, d, J=8.6Hz), 7.8-7.7 (2H, m), 7.6-7.3 (3H, m), 7.2-7.1 (2H m)，7.02 (2H，d，J=8.6Hz)，6.92 (1H，d，J=2.0Hz)，4.6-4.4 (1H，m), 114 (3H d J=2.4Hz), 1.11 (3H，d, J=2.4Hz)。 ’ ’ 奮施例1 8 ( 了1 3-[2-(N-異丙基苯磺醢胺基）-5-氯苯氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 103 3933 1 523506 A7 B7 五、發明説明（10Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.36 (nitroform: methanol = 9: 1); NM R: 5 8.11 (2H, d, J = 8.6Hz), 7.8-7.7 (2H, m) , 7.6-7.3 (3H, m), 7.2-7.1 (2H m), 7.02 (2H, d, J = 8.6Hz), 6.92 (1H, d, J = 2.0Hz), 4.6-4.4 (1H, m) , 114 (3H d J = 2.4Hz), 1.11 (3H, d, J = 2.4Hz). '' Fen Example 18 (1-3- [2- (N-Isopropylbenzenesulfonamido) -5-chlorophenoxymethyl] cinnamic acid This paper is in accordance with China National Standard (CNS) A4 specifications (210X297 mm) 103 3933 1 523506 A7 B7 V. Description of the invention (10

C〇〇H NM R ： δ 7.9-7.8 (2H, m), 7.73 (1 H, d, J=1 5.8Hz), 7.6-7.3 (5H, m), 7.2-7.0 (4H, m), 6.78 (1H, d, J=2.2Hz), 6.42 (1H, d, J=15.8Hz), 4.6-4.4 (1H, m), 1.17 (3H, d, J=6.8Hz), 1.13 (3H, d, J=6.8Hz)〇 丁 L C : R f 0.33 (氯仿：甲醇=9:1); --------— (請先閱讀背面之注意事項再填寫本頁) 審撫俐1 3 8) 4-[2-(H-異丙基苯磺醢胺基）-5-三氟甲基苯氧甲基]環己 烷酸C〇〇H NM R: δ 7.9-7.8 (2H, m), 7.73 (1 H, d, J = 1 5.8Hz), 7.6-7.3 (5H, m), 7.2-7.0 (4H, m), 6.78 (1H, d, J = 2.2Hz), 6.42 (1H, d, J = 15.8Hz), 4.6-4.4 (1H, m), 1.17 (3H, d, J = 6.8Hz), 1.13 (3H, d, J = 6.8Hz) 〇 LC: R f 0.33 (chloroform: methanol = 9: 1); --------— (Please read the precautions on the back before filling this page) Li Fu 1 3 8 ) 4- [2- (H-Isopropylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] cyclohexane acid

COOH T L C : R f 0.53 (氛仿：甲酵：乙酸：1 0 〇 : 5 : 1 ); NMR : δ 7.81 (2H, m), 7.42-7.63 (3H, m), 7.10-7.24 (3H, m)，4.38 (1H,七峯， J=6.8Hz), 3.79 (2H, m), 2.33 (1H, tt, J=3.8, 10.2Hz), 2.1 1 (2H, m), 1.93 (2H, m), 1.71 (1H, m), 1.50 (2H, m), 1.18 (2H, m), 1.07 (3H, d, J=6.8Hz), 1.02 (3H, d, J=6.8Hz), g 施例 1 8 ( 3 9 ) 4-[2-(N-異丙基苯磺釀胺基）-5-氯苯氧甲基]苯乙酸 訂COOH TLC: R f 0.53 (Aromatic imitation: Formazan: Acetic acid: 1 0 〇: 5: 1); NMR: δ 7.81 (2H, m), 7.42-7.63 (3H, m), 7.10-7.24 (3H, m ), 4.38 (1H, seven peaks, J = 6.8Hz), 3.79 (2H, m), 2.33 (1H, tt, J = 3.8, 10.2Hz), 2.1 1 (2H, m), 1.93 (2H, m) , 1.71 (1H, m), 1.50 (2H, m), 1.18 (2H, m), 1.07 (3H, d, J = 6.8Hz), 1.02 (3H, d, J = 6.8Hz), g Example 1 8 (3 9) 4- [2- (N-Isopropylbenzenesulfonylamino) -5-chlorophenoxymethyl] phenylacetate

經濟部中央標準局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS ) A4規格（210X：297公釐） 104 39331 523506 Μ Β7 五、發明説明（1 05)Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs This paper is sized for the Chinese National Standard (CNS) A4 (210X: 297 mm) 104 39331 523506 Μ B7 V. Description of the invention (1 05)

'C〇〇H NMR ： 5 7.9-7.8 (2H, m), 7.6-7.4 (3H, m), 7.28 (2H, d, J=7.4Hz), 7.13 (1H, d, J=8.6Hz), 7.01 (1H, dd, J=2.2, 8.6Hz), 6.89 (2H, d, J=8.6Hz), 6.78 (1H, d, J=2.2Hz)，4.6-4.4 (1H, m), 3.66 (2H, s)，1.15 (3H, s), 1·12 (3H，s)。 g ife m 18(40) (請先閱讀背面之注意事項再填寫本頁) 4-[2-(N-異丙基苯磺醢胺基）-5-三氟甲基苯氧甲基]桂皮 酸'C〇〇H NMR: 5 7.9-7.8 (2H, m), 7.6-7.4 (3H, m), 7.28 (2H, d, J = 7.4Hz), 7.13 (1H, d, J = 8.6Hz), 7.01 (1H, dd, J = 2.2, 8.6Hz), 6.89 (2H, d, J = 8.6Hz), 6.78 (1H, d, J = 2.2Hz), 4.6-4.4 (1H, m), 3.66 (2H , s), 1.15 (3H, s), 1.12 (3H, s). g ife m 18 (40) (Please read the precautions on the back before filling out this page) 4- [2- (N-Isopropylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamon acid

〇2S 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.5 (氛仿：甲醇=9 : 1); NM R ： δ 7.9-7.8 (3Η, m), 7.60 (2H, d, J=8.0Hz), 7,5-7.3 (5H, m), 7.3-7.2 (3H, m), 6.49 (1H, d, J=15.8Hz), 5.08 (2H, s), 4.4-4.3 (1H, m), 1.05 (6H, d, J=6.6Hz)〇 管施例1 S f ) 3-[4-[2-(N-異丙基苯磺醢胺基卜5-三氟甲基苯氧甲基]笨 基]丙酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 105 39 3 3 1 523506 A7 B7 五、發明説明（1 〇6)〇2S TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.5 (Aromatic imitation: methanol = 9: 1); NM R: δ 7.9-7.8 (3Η, m), 7.60 (2H, d, J = 8.0 Hz), 7,5-7.3 (5H, m), 7.3-7.2 (3H, m), 6.49 (1H, d, J = 15.8Hz), 5.08 (2H, s), 4.4-4.3 (1H, m) , 1.05 (6H, d, J = 6.6Hz) tube Example 1 S f) 3- [4- [2- (N-Isopropylbenzenesulfonamidob 5-trifluoromethylphenoxymethyl ] Benzyl] Propionate This paper is sized for the Chinese National Standard (CNS) A4 (210X 297 mm) 105 39 3 3 1 523506 A7 B7 V. Description of the invention (1 06)

T L C ： R f 0.59 (氯仿：甲醇=9 : 1 ); NM R ： δ 7.80 (2Η, d, J=7.4Hz), 7.5-7.4 (1 H, m), 7.4-7.2 (9Η, m), 4.99 (2H, s), 4.4-4.2 (1H, m), 3.00 (2H, t, J=7.6Hz), 2.72 (2H, t, J=7.6Hz), 1.08 (3H, d, J=6.8Hz), 1.02 (3H, d, J=6.8Hz)〇 奮_锎1 8 U2) 3-[2-N-異丙基苯磺醢胺基）-5-三氟甲基苯氧甲基）苯乙酸 (請先閲讀背面之注意事項再填寫本頁) F3TLC: R f 0.59 (chloroform: methanol = 9: 1); NM R: δ 7.80 (2Η, d, J = 7.4Hz), 7.5-7.4 (1 H, m), 7.4-7.2 (9Η, m), 4.99 (2H, s), 4.4-4.2 (1H, m), 3.00 (2H, t, J = 7.6Hz), 2.72 (2H, t, J = 7.6Hz), 1.08 (3H, d, J = 6.8Hz ), 1.02 (3H, d, J = 6.8Hz) 〇fen_ 锎 1 8 U2) 3- [2-N-Isopropylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl) benzene Acetic acid (Please read the notes on the back before filling this page) F3

Η 〇 〇 C 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.50 (氯仿：甲醇= 9:1); NMR ：δ7.8-7.7 (2H, m), 7.6-7.2 (10H, m), 5.05 (1H, d, J=11.0Hz), 4.98 (1H, d, J=11.0Hz), 4.4-4.2 (1 H, m), 3.68 (2H, s), 1.06 (3H, d, J=6.6Hz), 1.03 (3H, d, J=6.6Hz)〇 奮_例1 8 U 3 ) 4-[2-(N-異丙基-4-乙氧基苯磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 106 393 3 1 523506 A7 B7〇 〇C TLC printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.50 (chloroform: methanol = 9: 1); NMR: δ 7.8-7.7 (2H, m), 7.6-7.2 (10H, m) , 5.05 (1H, d, J = 11.0Hz), 4.98 (1H, d, J = 11.0Hz), 4.4-4.2 (1 H, m), 3.68 (2H, s), 1.06 (3H, d, J = 6.6Hz), 1.03 (3H, d, J = 6.6Hz). Example 1 8 U 3) 4- [2- (N-isopropyl-4-ethoxybenzenesulfonamido) -5- Trifluoromethylphenoxymethyl] benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X297 mm) 106 393 3 1 523506 A7 B7

02S 五、發明説明（ioi02S V. Description of Invention

C〇〇H 〇c2h5 T L C : R f 0.44 (氯仿··甲酵=9 : 1); NMR ： δ 8.1 5 (2H, d, J=8.2Hz), 7.71 (2H, d, J=8.8Hz), 7.54 (2H, d, J=8.2Hz), 7.3-7.2 (3H, m), 6.78 (2H, d, J=8.8Hz), 5.14 (2H, s), 4.4-4.2 (1H, m), 4.03 (2H, q, J=7.0Hz), 1.44 (3H, t, J=7.0Hz), 1.08 (3H, d, J=7.0Hz), 1.04 (3H, d, J=7.0Hz)〇 奩_例1 8 4-[2-(N-異丁基苯磺釀胺基）-5-甲基苯氧甲基]苯甲酸C〇H 〇c2h5 TLC: R f 0.44 (chloroform · formazan = 9: 1); NMR: δ 8.1 5 (2H, d, J = 8.2Hz), 7.71 (2H, d, J = 8.8Hz) , 7.54 (2H, d, J = 8.2Hz), 7.3-7.2 (3H, m), 6.78 (2H, d, J = 8.8Hz), 5.14 (2H, s), 4.4-4.2 (1H, m), 4.03 (2H, q, J = 7.0Hz), 1.44 (3H, t, J = 7.0Hz), 1.08 (3H, d, J = 7.0Hz), 1.04 (3H, d, J = 7.0Hz) 〇 奁 _ Example 1 8 4- [2- (N-Isobutylbenzenesulfonylamino) -5-methylphenoxymethyl] benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁) 〇 NIS Θ ΜCOOH (Please read the notes on the back before filling this page) 〇 NIS Θ Μ

Ρ 經濟部中央標準局員工消費合作社印製 T L C : R f 〇·47 (氯仿：甲醇：乙酸= i〇〇:5:l); NMR ： 5 8.07 (2H,d, J=8.2Hz), 7.63 (2H, m), 7.15-7.44 (6H, m), 6.79 (1H, m), 6.65 (1 H, m), 4.80 (2H, m), 3.40 (2H, m), 2.33 (3H, s), 1.63 (1 H, m), 0.90 (6H, d, J=6.4Hz)〇 奮）fe 例 i 8 u pn 4-[2-(N-異丙基苯磺醢胺基）-5-氟苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) Α4規格（210&gt;&lt; 297公釐） 107 3933 1 523506 A7 B7 五、發明説明（10设Ρ TLC printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: R f 〇 47 (chloroform: methanol: acetic acid = 〇〇: 5: l); NMR: 5 8.07 (2H, d, J = 8.2Hz), 7.63 (2H, m), 7.15-7.44 (6H, m), 6.79 (1H, m), 6.65 (1 H, m), 4.80 (2H, m), 3.40 (2H, m), 2.33 (3H, s) , 1.63 (1 H, m), 0.90 (6H, d, J = 6.4Hz) 〇fen) fe Example i 8 u pn 4- [2- (N-isopropylbenzenesulfonamido) -5-fluoro Phenoxymethyl] benzoic acid This paper is in accordance with China National Standard (CNS) A4 specification (210 &gt; &lt; 297 mm) 107 3933 1 523506 A7 B7 V. Description of the invention (10 design

COOH (請先閱讀背面之注意事項再填寫本頁) NMR (DMSO-d6) ：δ 7.95 (2Η, d, J=8.2Hz), 7.80 (2H, d, J=7.2Hz), 7.46-7.65 (5H, m), 7.08 (2H, m), 6.82 (1H, m), 5.14 (2H, bs), 4.20 (1H, t*, J=6.6Hz), 0.94 (6H, d, J=6.6Hz)〇 管施例18 (46) 4-[2-(H-異丙基苯磺醢胺基）-5-甲氧基苯氧甲基]苯甲酸COOH (Please read the notes on the back before filling this page) NMR (DMSO-d6): δ 7.95 (2Η, d, J = 8.2Hz), 7.80 (2H, d, J = 7.2Hz), 7.46-7.65 ( 5H, m), 7.08 (2H, m), 6.82 (1H, m), 5.14 (2H, bs), 4.20 (1H, t *, J = 6.6Hz), 0.94 (6H, d, J = 6.6Hz) 〇Example 18 (46) 4- [2- (H-Isopropylbenzenesulfonamido) -5-methoxyphenoxymethyl] benzoic acid

COOH 經濟部中央標準局員工消費合作社印製COOH Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

NMR (DMSO-d6) ：δ 7.95 (2Η, d, J=8.2Hz), 7.73 (2H, d, J=7.2Hz), 7.42-7.68 (3H, m), 6.93 (2H, d, J=8.6Hz), 7.21 (1 H, m), 6.56 (2H, dd, J=8.6Hz, J=2.8Hz), 5.11 (2H，bs), 4.20 (1H,七峯，J=6.6Hz), 3.79 (3H, s), 0.94 (6H, d, J=6.6Hz)。 管施例1 8 (47 ) 4-[2-(N-丙基笨磺醢胺基）-5-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 108 3 93 3 1 523506 A7 B7 五、發明説明（lod 〇^σNMR (DMSO-d6): δ 7.95 (2Η, d, J = 8.2Hz), 7.73 (2H, d, J = 7.2Hz), 7.42-7.68 (3H, m), 6.93 (2H, d, J = 8.6 Hz), 7.21 (1 H, m), 6.56 (2H, dd, J = 8.6Hz, J = 2.8Hz), 5.11 (2H, bs), 4.20 (1H, seven peaks, J = 6.6Hz), 3.79 ( 3H, s), 0.94 (6H, d, J = 6.6Hz). Example 1 8 (47) 4- [2- (N-propylbenzylsulfonamido) -5-methylphenoxymethyl] benzoic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 Mm) 108 3 93 3 1 523506 A7 B7 V. Description of the invention (lod 〇 ^ σ

COOH N〆COOH N〆

02S T L C : R f 0.38 (氯仿：甲醇：乙酸=100:5:1); NMR ： 5 8.07 (2H,d, J=8.6Hz), 7.67 (2H, m), 7.15-7.45 (6H, m), 6.79 (1H, m), 6.68 (1 H, m), 4.83 (2H, brs), 3.57 (2H, m), 2.34 (3H, s), 1.48 (2H, m), 0.88 (3H, t, J=7.4Hz)〇 簠施_例18(48) 4-[2-[N-(丙-2-烯基）苯磺醢胺基]-5-甲基苯氧甲基]苯甲 酸02S TLC: R f 0.38 (chloroform: methanol: acetic acid = 100: 5: 1); NMR: 5 8.07 (2H, d, J = 8.6Hz), 7.67 (2H, m), 7.15-7.45 (6H, m) , 6.79 (1H, m), 6.68 (1 H, m), 4.83 (2H, brs), 3.57 (2H, m), 2.34 (3H, s), 1.48 (2H, m), 0.88 (3H, t, J = 7.4Hz) Example 18 (48) 4- [2- [N- (prop-2-enyl) benzenesulfonamido] -5-methylphenoxymethyl] benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

MeMe

NN

02S 經濟部中央標準局員工消費合作社印製 TLC ： R f 0.39 (氯仿：甲醇：乙酸=100:5:1); NMR ： 5 8.07(2H,d, J=8.0Hz), 7.69 (2H, m), 7.13-7.48 (6H,m),6.78 (1H, m), 6.66 (1H, m), 5.80 (1H,tdd, J=6.2, 10.2, 17.2Hz), 4.98-5^1 2 (2H, m), 4.84 (2H, brs), 4.23 (2H, m), 2·33 (3H, s)。 奮施例1 8 ( 4 9 ) 4-[2-[N-(2-甲基丙-2-烯基）苯磺醸胺基]-5-甲基苯氧甲 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 109 3933 102S Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.39 (chloroform: methanol: acetic acid = 100: 5: 1); NMR: 5 8.07 (2H, d, J = 8.0Hz), 7.69 (2H, m ), 7.13-7.48 (6H, m), 6.78 (1H, m), 6.66 (1H, m), 5.80 (1H, tdd, J = 6.2, 10.2, 17.2Hz), 4.98-5 ^ 1 2 (2H, m), 4.84 (2H, brs), 4.23 (2H, m), 2.33 (3H, s). Fen Shi Example 1 8 (4 9) 4- [2- [N- (2-methylprop-2-enyl) benzenesulfonamido] -5-methylphenoxymethyl This paper applies Chinese national standards (CNS) A4 size (210X297 mm) 109 3933 1

C〇〇H 523506 A7 B7 五、發明説明（1 1 0) 基]苯甲酸 u T L C : R f 0.37 (氯仿：甲醇：乙酸=100:5:1); NM R ： δ 8.07 (2H, d, J=8.2Hz), 7.66 (2H, m), 7.16-7.47 (6H, m), 6.77 (1 H, m), 6.64 (1 H, m), 4.80 (2H, brs), 4.71 (2H, m), 4.20 (1 H, brs), 2.32 (3H, s), 1.77 (3H, S)〇 奮施例18 (50) 4-[2-(N -環丙基甲基苯磺釀胺基）-5-甲基苯氧甲基]苯甲 酸 (請先閱讀背面之注意事項再填寫本頁)C〇H 523506 A7 B7 V. Description of the invention (1 1 0) yl] benzoic acid u TLC: R f 0.37 (chloroform: methanol: acetic acid = 100: 5: 1); NM R: δ 8.07 (2H, d, J = 8.2Hz), 7.66 (2H, m), 7.16-7.47 (6H, m), 6.77 (1 H, m), 6.64 (1 H, m), 4.80 (2H, brs), 4.71 (2H, m ), 4.20 (1 H, brs), 2.32 (3H, s), 1.77 (3H, S). Example 18 (50) 4- [2- (N-cyclopropylmethylbenzenesulfonylamino) -5-methylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

Me Ό； 〇jaMe Ό; 〇ja

C〇〇H hr 〇2s 經濟部中央標準局員工消費合作社印製 TLC ： R f 0.31 (氯仿：甲醇：乙酸=100:5:1); NM R ： δ 8.06 (2H, d, J=8.0Hz), 7.68 (2H, m), 7.18-7.44 (6H, m), 6.80 (1 H, m), 6.68 (1 H, m), 4.84 (2H, brs), 3.48 (2H, m), 2.34 (3H, s)；O.91 (1 H, m), 0.38 (2H, m),0_07 (2H，m)。 g as gll 1 8 f B 1 ) 4-[2-(N-丙基笨磺釀胺基）-5-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 110 3933 1 523506 A7 B7 五、發明説明（1 1 ])C〇H hr 〇2s TLC printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.31 (chloroform: methanol: acetic acid = 100: 5: 1); NM R: δ 8.06 (2H, d, J = 8.0Hz ), 7.68 (2H, m), 7.18-7.44 (6H, m), 6.80 (1 H, m), 6.68 (1 H, m), 4.84 (2H, brs), 3.48 (2H, m), 2.34 ( 3H, s); 0.91 (1 H, m), 0.38 (2H, m), 0_07 (2H, m). g as gll 1 8 f B 1) 4- [2- (N-propylbenzylsulfonylamino) -5-chlorophenoxymethyl] benzoic acid The paper size applies to Chinese National Standard (CNS) A4 specification (210X297 Mm) 110 3933 1 523506 A7 B7 V. Description of the invention (1 1))

CICI

NIS 2 〇NIS 2 〇

PP

C〇〇H T L C : R f 0·32 (氯仿：甲醇=20:1); NMR ： δ 8.07 (2Η, d, J=7.8Hz), 7.64 (2H, d, J=6.8Hz), 7.10-7.41 (6H, m), 6.85-6.99 (2H, m), 4.82 (2H, bs), 3.55 (2H, t, J=6.8Hz), 1.35-1.52 (2H, m), 0.87 (3H, t, J=7.6Hz)〇 (諸先閲讀背面之注意事項再填寫本頁) 4-[2-(H-異丁基苯磺醣胺基）-5-氯苯氧甲基]苯甲酸C〇HTLC: R f 0.32 (chloroform: methanol = 20: 1); NMR: δ 8.07 (2Η, d, J = 7.8Hz), 7.64 (2H, d, J = 6.8Hz), 7.10-7.41 (6H, m), 6.85-6.99 (2H, m), 4.82 (2H, bs), 3.55 (2H, t, J = 6.8Hz), 1.35-1.52 (2H, m), 0.87 (3H, t, J = 7.6Hz) 〇 (Please read the precautions on the back before filling out this page)

經濟部中央標準局員工消費合作社印製 T L C : R f 〇.32 (氯仿：甲醇= 20:1); NMR ： δ 8.04 (2H, d, J=7.8Hz), 7.54 (2H, d, J=7.4Hz), 7.10-7.41 (6H, m), 6.80-7.01 (2H, m), 4.58-4.95 (2H, bs), 3.34 (2H, d, J=7.0Hz), 1.46-1.65 (1 H, m), 0.83 (6H, d, J=6.4Hz)〇 ' 管施例1 8 ( 5 4-[2-(H-丙-2-烯基）苯磺醢胺基]-5-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 111 3933 1 523506 A7 B7 五、發明説明（11^)Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.32 (chloroform: methanol = 20: 1); NMR: δ 8.04 (2H, d, J = 7.8Hz), 7.54 (2H, d, J = 7.4Hz), 7.10-7.41 (6H, m), 6.80-7.01 (2H, m), 4.58-4.95 (2H, bs), 3.34 (2H, d, J = 7.0Hz), 1.46-1.65 (1 H, m), 0.83 (6H, d, J = 6.4Hz) 0 'Tube Example 1 8 (5 4- [2- (H-prop-2-enyl) benzenesulfonamido] -5-chlorophenoxy Methyl] benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X 297 mm) 111 3933 1 523506 A7 B7 V. Description of the invention (11 ^)

COOH 〇 NIS 〈02COOH 〇 NIS 〈02

CICI

丁 L C : R f 0·30 (氯仿：甲醇=20:1); NMR ： δ 8.09 (2Η, d, J=8.2Hz), 7.68 (2H, d, J=6.8Hz), 7.19-7.52 (6H, m), 6.87-7.01 (2H, m), 5.76 (1H, ddt, J=17.2Hz, 9.8Hz, 6.4Hz) 5.09 (1H, d, J=17·2Ηζ), 5·07 (1H ,d , J=9.8Hz), 4·85 (2H，s), 4.21 (2H, d, J=6.4Hz)。 奮淪例1 8 (fU ) 4-[2-[N-(2-甲基丙-2-烯基）苯磺醸胺基卜5-氯苯氧甲基] 笨甲酸 (請先閱讀背面之注意事項再填寫本頁)DLC: R f 0 · 30 (chloroform: methanol = 20: 1); NMR: δ 8.09 (2Η, d, J = 8.2Hz), 7.68 (2H, d, J = 6.8Hz), 7.19-7.52 (6H , m), 6.87-7.01 (2H, m), 5.76 (1H, ddt, J = 17.2Hz, 9.8Hz, 6.4Hz) 5.09 (1H, d, J = 17 · 2Ηζ), 5.07 (1H, d , J = 9.8Hz), 4.85 (2H, s), 4.21 (2H, d, J = 6.4Hz). Example 1 8 (fU) 4- [2- [N- (2-methylprop-2-enyl) benzenesulfonamidob 5-chlorophenoxymethyl] stearic acid (Please read the (Please fill in this page again)

經濟部中央標準局員工消費合作社印t TLC ： R f 0.33 (氯仿：甲醇= 20:1); NMR ： δ 8.09 (2Η, d, J=8.2Hz), 7.65 (2H, d, J=6.8Hz), 7.21-7.51 (6H, m), 6.83-7.00 (2H, m), 4.81 (2H, s), 4.74 (1 H, s), 4.68 (1 H, s), 4.18 (2H,s), 1.75 (3H, s)〇 、 審 _ 例 1 5 ΡΠ 4-[2-(N-環丙基甲基磺醣胺基）-5-氯苯氧甲基]苯甲酸 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 112 3933 1 523506 A7 B7 五、發明説明（11TLC: R f 0.33 (chloroform: methanol = 20: 1); NMR: δ 8.09 (2Η, d, J = 8.2Hz), 7.65 (2H, d, J = 6.8Hz ), 7.21-7.51 (6H, m), 6.83-7.00 (2H, m), 4.81 (2H, s), 4.74 (1 H, s), 4.68 (1 H, s), 4.18 (2H, s), 1.75 (3H, s) 〇 Examination Example 5 5 ΠΠ 4- [2- (N-cyclopropylmethylsulfosylamino) -5-chlorophenoxymethyl] benzoic acid The paper size is applicable to China Standard (CNS) A4 specification (210X297 mm) 112 3933 1 523506 A7 B7 V. Description of invention (11

CI Ό：CI Ό:

XTXT

C〇〇H o2s 丁 L C : R f 0·40 (氯仿：甲醇=20:1); NMR ： δ 8.07 (2H, d, J=8.6Hz), 7.69 (2H, d, J=7.0Hz), 7.20-7.48 (6H, m), 6.85-7.09 (2H, m), 4.85(2H, s), 3.47 (2H, bs), 0.85 (1 H, m), 0.38 (2H, m), 0.06 (2H, m)〇 奮 _ 例 1 8 ( 5 fi ) 5-[2-(N-異丙基苯磺醢胺基）-5-甲基苯氧甲基]呋喃-2-羧 酸 .. 在 ΙΓ\C〇〇 o 2s butyl LC: R f 0 · 40 (chloroform: methanol = 20: 1); NMR: δ 8.07 (2H, d, J = 8.6Hz), 7.69 (2H, d, J = 7.0Hz), 7.20-7.48 (6H, m), 6.85-7.09 (2H, m), 4.85 (2H, s), 3.47 (2H, bs), 0.85 (1 H, m), 0.38 (2H, m), 0.06 (2H , m) 〇fen_ Example 1 8 (5 fi) 5- [2- (N-Isopropylbenzenesulfonamido) -5-methylphenoxymethyl] furan-2-carboxylic acid. \

C〇〇H o2s 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) Τ L C ： R f 0.18 (氯仿：甲醇=9:1); NM R : δ 7.82 (2H, m), 7.56-7.35 (3H, m)，7.31 (1 H，d，J =3·5Ηζ)，6.97 (1 H, d, J=8.5Hz), 6.83-6.75 (2H, m), 6.63 (1 H, d, J=3.5Hz), 5.03 (1 H, d, J=1 4Hz), 4.98 (1H, d, J=14Hz), 4.37 (1H, m) , 2.37 (3H, s), 1.09-0.96 (6H, m)〇 g _ 例 1 8 ( 5 7 ) 4-[2-(H-甲氧甲基苯磺醸胺基）-5-三氟甲基苯氧甲基]苯 甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 113 3933 1 523506 A7 B7 五、發明説明（11$C〇〇 o 2s Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Τ LC: R f 0.18 (chloroform: methanol = 9: 1); NM R: δ 7.82 ( 2H, m), 7.56-7.35 (3H, m), 7.31 (1 H, d, J = 3.5Ηζ), 6.97 (1 H, d, J = 8.5Hz), 6.83-6.75 (2H, m), 6.63 (1 H, d, J = 3.5Hz), 5.03 (1 H, d, J = 1 4Hz), 4.98 (1H, d, J = 14Hz), 4.37 (1H, m), 2.37 (3H, s) , 1.09-0.96 (6H, m) 〇g _ Example 1 8 (5 7) 4- [2- (H-methoxymethylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzene Formic acid size of paper is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) 113 3933 1 523506 A7 B7 V. Description of the invention (11 $

C〇〇H N 〇Me 〇2S、 ΌC〇〇H 〇Me 〇2S, Ό

T L C : R f 0·45 (氯仿：甲醇··乙酸=100:5:1); NMR ：δ8.09 (2H, d, J=8.0Hz), 7.65 (2H, m), 7.43-7.53 (2H, m), 7.20-7.40 (5H, m), 7·11 (1H, m), 5.09 (2H，s), 4.89 (2H, s), 3·44 (3H, s)。 音嫵锎1 8 ( 5 8 )4-[2-(N-異丙基-2-α吩基磺醯胺基）-5-氯苯氧甲基）苯甲 酸 COOHTLC: R f 0 · 45 (chloroform: methanol · acetic acid = 100: 5: 1); NMR: δ 8.09 (2H, d, J = 8.0Hz), 7.65 (2H, m), 7.43-7.53 (2H , m), 7.20-7.40 (5H, m), 7.11 (1H, m), 5.09 (2H, s), 4.89 (2H, s), 3.44 (3H, s). Tone 1 8 (5 8) 4- [2- (N-Isopropyl-2-αphenylsulfonamido) -5-chlorophenoxymethyl) benzoic acid COOH

(請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 丁乙（：：1^0_34(氯仿：甲醇=2 0:1); NMR ：δ8.14 (2Η, d, J=8.2Hz), 7.52-7.57 (4H, m), 6.98-7.03 (4H, m), 5.12 (2H, s), 4·55 (1H,七峯，J=6.4Hz)，1 ·09 (6H, d, J=6.6Hz)。 董…施例18 (59)4-[2-(N-異丙基-2-«吩磺醢胺基）-5-甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 114 3 933 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（11 5)(Please read the notes on the back before filling this page) Ding Yi (:: 1 ^ 0_34 (chloroform: methanol = 2 0: 1); NMR: δ8.14 (2Η, d, J = 8.2Hz), 7.52-7.57 (4H, m), 6.98-7.03 (4H, m), 5.12 (2H, s), 4.55 (1H, seven peaks, J = 6.4Hz), 1 · 09 (6H, d, J = 6.6Hz). Dong ... Example 18 (59) 4- [2- (N-isopropyl-2- «phensulfonamido) -5-methylphenoxymethyl ] Benzoic acid The paper size is in accordance with Chinese National Standard (CNS) A4 (210X 297 mm) 114 3 933 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (11 5)

COOH T L C : R f 0.39 (氛仿：甲醇= 20:1); NM R ： δ 8.1 3 (2Η, d, J=8.2Hz),7.43-7.58 (4H, m), 6.97 (1 H, m), 6.80 (2H, m), 5·12 (2H, s), 4·45 (1H,七峯，J=6.4Hz), 1.09 (6H，d, J=6.6Hz)。 奮嫵俐1 8 (60) 4- [2- (N-異丙基 酸 呋喃基磺釀胺基卜5-甲基笨氧甲基]苯甲COOH TLC: R f 0.39 (mfd: methanol = 20: 1); NM R: δ 8.1 3 (2Η, d, J = 8.2Hz), 7.43-7.58 (4H, m), 6.97 (1 H, m) , 6.80 (2H, m), 5.12 (2H, s), 4.45 (1H, seven peaks, J = 6.4Hz), 1.09 (6H, d, J = 6.6Hz). Fen Lili 1 8 (60) 4- [2- (N-isopropyl acid furanylsulfonylaminomethyl 5-methylbenzyloxymethyl) benzyl

COOH 丁 L C : R ί 0.42 (氯仿：甲醇：乙酸=1〇〇:5:1); NMR ： 5 8.14 (2Η, d, J=8.2Hz), 7.58 (2H, d, J=8.2Hz), 7.44 (1H, dd, J=0.8, 1.6Hz), 6.88-6.95 (2H, m), 6.72-6.82 (2H, m), 6.41 (1H,dd, J=1.6, 3.4Hz), 5.12 (2H,s), 4.51 (1H,t 峯，J=6.6Hz)，2.31 (3H，s)，1.12 (3H,d, J=6_6Hz), 1.10 (3H, d, J=6.6Hz)〇 當淪锎18 (61) 4-[2-(H-異丙基-2-呋喃基磺醵胺基）-卜氯苯氧甲基]笨甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 115 393 3 1 (請先閱讀背面之注意事項再填寫本頁) 523506 A7 B7 五、發明説明（11^)COOH butyl LC: R ί 0.42 (chloroform: methanol: acetic acid = 1OO: 5: 1); NMR: 5 8.14 (2Η, d, J = 8.2Hz), 7.58 (2H, d, J = 8.2Hz), 7.44 (1H, dd, J = 0.8, 1.6Hz), 6.88-6.95 (2H, m), 6.72-6.82 (2H, m), 6.41 (1H, dd, J = 1.6, 3.4Hz), 5.12 (2H, s), 4.51 (1H, t peak, J = 6.6Hz), 2.31 (3H, s), 1.12 (3H, d, J = 6_6Hz), 1.10 (3H, d, J = 6.6Hz) (61) 4- [2- (H-Isopropyl-2-furylsulfonamido) -chlorochlorophenoxy] benzic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X 297) PCT) 115 393 3 1 (Please read the notes on the back before filling out this page) 523506 A7 B7 V. Description of the invention (11 ^)

COOHCOOH

丁1(3:1^0.43(氯仿：甲醇：乙酸=100:5:1); ： NMR ： δ 8.16 (2H, d, J=8.4Hz), 7.57 (2H, d, J=8.4Hz), 7.45 (1 H, dd, J=0.8, 1.6Hz), 6.95-7.04 (3H, m), 6.92 (1H, d, J=4.4Hz), 6.43 (1H, dd, J=1.8, 3.4Hz), 5·13 (2H, s)，4.49 (1H，七峯，J=7.0Hz), 1.11 (3H, d, J=7.0Hz), 1.09 (3H, d, J=7.0Hz)〇 奮施例18 (62) 4-[2-(N-異丁基笨磺醢胺基）-4-甲基苯氧甲基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)Ding 1 (3: 1 ^ 0.43 (chloroform: methanol: acetic acid = 100: 5: 1);: NMR: δ 8.16 (2H, d, J = 8.4Hz), 7.57 (2H, d, J = 8.4Hz), 7.45 (1 H, dd, J = 0.8, 1.6Hz), 6.95-7.04 (3H, m), 6.92 (1H, d, J = 4.4Hz), 6.43 (1H, dd, J = 1.8, 3.4Hz), 5.13 (2H, s), 4.49 (1H, seven peaks, J = 7.0Hz), 1.11 (3H, d, J = 7.0Hz), 1.09 (3H, d, J = 7.0Hz). Example 18 (62) 4- [2- (N-Isobutyl benzylsulfonamido) -4-methylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 T L C : R f 0.23 (己烷：乙酸乙酯=1 : 1); NM R ： δ 8.06 (2Η, d, J=8Hz), 7.65-7.61 (2H, m), 7.6-7.4 (7H, m), 6.71 (1 H, d, J=8Hz), 4.9-4.6 (2H, m), 3.5-3.4 (2H, m), 2.29 (3H, s), 1.63 (1H, , J=6.5 Hz), 0.91 (6H, d, J=6.5Hz)〇 奮 _ 例 1 8 ( fi 3) 4-[2-(N-異丙基苯磺醢胺基）-4-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） λ 116 39331Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.23 (hexane: ethyl acetate = 1: 1); NM R: δ 8.06 (2Η, d, J = 8Hz), 7.65-7.61 (2H, m ), 7.6-7.4 (7H, m), 6.71 (1 H, d, J = 8Hz), 4.9-4.6 (2H, m), 3.5-3.4 (2H, m), 2.29 (3H, s), 1.63 ( 1H,, J = 6.5 Hz), 0.91 (6H, d, J = 6.5Hz). Example 1 8 (fi 3) 4- [2- (N-isopropylbenzenesulfonamido) -4- Methylphenoxymethyl] benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X 297 mm) λ 116 39331

523506 Α7 Β7 五、發明説明（1 17)523506 Α7 Β7 V. Description of the invention (1 17)

COOH T L C ： R f 0.22 (己烷：乙酸乙酯=1:1); NMR ： 5 8.12 (2H,d, J=8Hz), 7.86-7.81 (2H, m), 7.52-7.30 (5H, m), 7.15-7.10 (1H, m), 6.94 (1H, d, J=1.5Hz), 6.84 (1H, d, J=8Hz), 5.02 (2H, s), 4.37 (1H, 七峯，J=6.5 Hz), 2.28 (3H, s), 1 ·08 (6H, t, J=6.5 Hz)。 奮遍例1 8 (fU) 4-[2-[N-(丙-2-烯基）苯磺釀胺基）-4-甲基苯氧甲基]苯甲 (請先閲讀背面之注意事項再填寫本頁) 酸 ΧίCOOH TLC: R f 0.22 (hexane: ethyl acetate = 1: 1); NMR: 5 8.12 (2H, d, J = 8Hz), 7.86-7.81 (2H, m), 7.52-7.30 (5H, m) , 7.15-7.10 (1H, m), 6.94 (1H, d, J = 1.5Hz), 6.84 (1H, d, J = 8Hz), 5.02 (2H, s), 4.37 (1H, seven peaks, J = 6.5 Hz), 2.28 (3H, s), 1 · 08 (6H, t, J = 6.5 Hz). Example 1 8 (fU) 4- [2- [N- (prop-2-enyl) benzenesulfonylamino) -4-methylphenoxymethyl] benzyl (Please read the notes on the back first (Fill in this page again)

COOHCOOH

NN

〇2S 丁 L C : R f 0.43 (氯仿：甲醇：乙酸=100:5:1); 經濟部中央標準局員工消費合作社印製 NM R (DMSO-d6) ： δ 7.89 (2Η, d, J=8.2Hz), 7.63 (2H, m), 7.38-7.59 (3H, m), 7.23 (2H, d, J=8.2Hz), 7.1 2 (1 H, dd, J=1.8, 8.4Hz), 6.98 (1 H, d, J=1.8Hz), 6.94 (1H, d, J=8.6Hz), 5.71 (1H, tdd, J=6.4, 10.0, 17.2Hz), 4.97-5.13 (2H, m), 4.88 (2H, brs), 4.17 (2H, m), 2.22 (3H，s)。 奮施例1 8 ( 5) 4-[2-(N-異丙基-4-乙氧基苯磺醢胺基）-5-氯苯氧甲基]_ 甲酸 本紙張尺度適用中關家標準（⑽）Μ規格（训χ2嘯 3933 1 523506 A7 B7 五、發明説明（1〇2S DLC: R f 0.43 (chloroform: methanol: acetic acid = 100: 5: 1); NM R (DMSO-d6) printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: δ 7.89 (2Η, d, J = 8.2 Hz), 7.63 (2H, m), 7.38-7.59 (3H, m), 7.23 (2H, d, J = 8.2Hz), 7.1 2 (1 H, dd, J = 1.8, 8.4Hz), 6.98 (1 H, d, J = 1.8Hz), 6.94 (1H, d, J = 8.6Hz), 5.71 (1H, tdd, J = 6.4, 10.0, 17.2Hz), 4.97-5.13 (2H, m), 4.88 (2H , brs), 4.17 (2H, m), 2.22 (3H, s). Example 1 8 (5) 4- [2- (N-Isopropyl-4-ethoxybenzenesulfonamido) -5-chlorophenoxymethyl] _ Formic acid This paper is applicable to Zhongguanjia standard (⑽) M specifications (Teaching 2 Xiao 3933 1 523506 A7 B7 V. Description of the invention (1

NM R ： δ 8.13 (2Η, d, ϋ=8.6Ηζ), 7.69 (2Η, d, J=9.0Hz), 7.49 (2H, d, J=8.6Hz), 6.97-7.09 (3H, m), 6.76 (2H, d, J=9.0Hz), 5.06 (2H, s), 4.34 (1 H,七峯:,J=6.6Hz), 4.02 (2H, q, J=7.2Hz), 1.43 (3H, t, J=7.0Hz), 1.06 (3H, d, J=6.6Hz), 1.03 (3H, d, J=6.6Hz)〇 奮）fe 锎 1 fUfifi) 4-[2-(N -異丙基-4-乙氧基苯磺醢胺基）-5 -甲基苯氧甲基]苯 甲酸NM R: δ 8.13 (2Η, d, ϋ = 8.6Ηζ), 7.69 (2Η, d, J = 9.0Hz), 7.49 (2H, d, J = 8.6Hz), 6.97-7.09 (3H, m), 6.76 (2H, d, J = 9.0Hz), 5.06 (2H, s), 4.34 (1 H, seven peaks :, J = 6.6Hz), 4.02 (2H, q, J = 7.2Hz), 1.43 (3H, t , J = 7.0Hz), 1.06 (3H, d, J = 6.6Hz), 1.03 (3H, d, J = 6.6Hz) 〇fen) fe 锎 1 fUfifi) 4- [2- (N -isopropyl- 4-ethoxybenzenesulfonamido) -5 -methylphenoxymethyl] benzoic acid

經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) NM R ： δ 8.1 2 (2Η, d, J=8.4Hz), 7.72 (2H, d, J=8.6Hz), 7.50 (2H, d, J=8.6Hz), 7.01 (1 H, d, J=8.8Hz)，6.72-6.80 (4H, m), 5.07 (2H, s)，4.34 (1 H,七峯，J=6_6Hz), 4.01 (2H, q, J=7.0Hz), 2.36 (3H, s), 1.42 (3H, t, J=6.8Hz), 1.07 (3H, d, J=7.2Hz), 1.04 (3H, d, J=6.8Hz)〇 y _ 例 (tm 4-[2-(N-乙基苯磺醸胺基）-4-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 118 3933 1 523506 A7 B7 五、發明説明（11Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) NM R: δ 8.1 2 (2Η, d, J = 8.4Hz), 7.72 (2H, d, J = 8.6Hz ), 7.50 (2H, d, J = 8.6Hz), 7.01 (1 H, d, J = 8.8Hz), 6.72-6.80 (4H, m), 5.07 (2H, s), 4.34 (1 H, seven peaks , J = 6_6Hz), 4.01 (2H, q, J = 7.0Hz), 2.36 (3H, s), 1.42 (3H, t, J = 6.8Hz), 1.07 (3H, d, J = 7.2Hz), 1.04 (3H, d, J = 6.8Hz) 〇y _ Example (tm 4- [2- (N-ethylbenzenesulfonamido) -4-methylphenoxymethyl] benzoic acid This paper is applicable to China Standard (CNS) A4 specification (210X297 mm) 118 3933 1 523506 A7 B7 V. Description of the invention (11

C〇〇H j〇cC〇〇H j〇c

ITIT

02S 丁LC : R f 〇.33 (氯仿：甲醇= 9:1); NMR ： 5 8.05 (2H, d, J=8.4Hz), 7.8-7.6 (2H, m), 7.4-7.2 (5H, m), 7.2-7.0 (2H, m), 6.75 (1 H, d, J=8.4Hz), 4.82 (2H, s), 3.8-3.6 (2H, m), 2.30 (3H, s), 1.11 (3H, t, J=7.0Hz)〇 音瀹锎1 8 (68) 4-[2-(H-丙基苯磺釀胺基）-4-甲基苯氧甲基]苯甲酸02S DLC: R f 0.33 (chloroform: methanol = 9: 1); NMR: 5 8.05 (2H, d, J = 8.4Hz), 7.8-7.6 (2H, m), 7.4-7.2 (5H, m ), 7.2-7.0 (2H, m), 6.75 (1 H, d, J = 8.4Hz), 4.82 (2H, s), 3.8-3.6 (2H, m), 2.30 (3H, s), 1.11 (3H , t, J = 7.0Hz) 〇 瀹 锎 瀹 锎 1 8 (68) 4- [2- (H-propylbenzenesulfonylamino) -4-methylphenoxymethyl] benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

、1T Ν', 1T Ν '

02S -1% 經濟部中央標準局員工消費合作社印製 TLC : R f 0.44 (氛仿：甲醇=9 : 1); NM R ： δ 8.05 (2Η, d, J=8.0Hz), 77-7.6 (2H, m), 7.5-7.0 (7H, m), 6.74 (1 H, d, J=8.4Hz), 4.80 (2H, s), 3.7-3.5 (2H, m), 2.29 (3H, s), 1.6-1.4 (2H, m), 0.89 (3H, t, J=7.4Hz)〇 , g _ 例 18 (69) 4-[2-(N-丁基苯磺醢胺基）-4-甲基苯氧甲基]笨甲酸 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 119 3933102S -1% Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.44 (Diffuse: methanol = 9: 1); NM R: δ 8.05 (2Η, d, J = 8.0Hz), 77-7.6 ( 2H, m), 7.5-7.0 (7H, m), 6.74 (1 H, d, J = 8.4Hz), 4.80 (2H, s), 3.7-3.5 (2H, m), 2.29 (3H, s), 1.6-1.4 (2H, m), 0.89 (3H, t, J = 7.4Hz) 〇, g _ Example 18 (69) 4- [2- (N-butylbenzenesulfonamido) -4-methyl Phenoxymethyl] stearic acid This paper is sized for China National Standard (CNS) A4 (210X 297 mm) 119 39331

MeMe

523506 Α7 Β7 五、發明説明（12() N〆523506 Α7 Β7 V. Description of the invention (12 () N〆

II

02S 丁 L C : R ί 0·49 (氛仿··甲醇=9 : 1); NMR ： 5 8.05 (2Η, d, J=8.2Hz), 77-7.6 (2H, m), 7.4-7.2 (5H, m), 7.2-7.0 (2H, m), 6.74 (1H, d, J=8.4Hz), 4.80 (2H, s), 3.7-3.5 (2H, m), 2.30 (3H, s), 1.6-1.2 (4H, m), 0.85 (3H, t，J=7.0Hz)。 g 施例 18 (70) 4-[2-[N-(2-甲基丙-2-烯基）苯磺釀胺基]-4-甲基苯氧甲 基]苯甲酸 (請先閲讀背面之注意事項再填寫本頁)02S DLC: R ί 0 · 49 (methanol · 9 = 1); NMR: 5 8.05 (2Η, d, J = 8.2Hz), 77-7.6 (2H, m), 7.4-7.2 (5H , m), 7.2-7.0 (2H, m), 6.74 (1H, d, J = 8.4Hz), 4.80 (2H, s), 3.7-3.5 (2H, m), 2.30 (3H, s), 1.6- 1.2 (4H, m), 0.85 (3H, t, J = 7.0Hz). g Example 18 (70) 4- [2- [N- (2-methylprop-2-enyl) benzenesulfonylamino] -4-methylphenoxymethyl] benzoic acid (please read the back first (Notes for filling in this page)

經漓部中央標準局員工消費合作社印製 TLC : R f 0.38 (氯仿：甲醇=9:1); NMR ： δ 8.06 (2Η, d, J=8Hz), 7.65 (2H, m), 7.47-7.25 (3H, m), 7.19 (2H, d, J=8Hz), 7.13 (1 H, d, J=2Hz), 7.04 (1 H, dd, J=8 A 2Hz), 6.70 (1 H, d, J=8Hz), 4.85-4.65 (4H, m), 4.21 (2H, s), 2.29 (3H, s), 1.78 (3H, s)〇 謇遍锎1 8 (71) 4-[2-(N-環丙基甲基苯磺醢胺基）-4-甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） 120 3933 1 523506 A7 B7 五、發明説明（121)Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of TLC: R f 0.38 (chloroform: methanol = 9: 1); NMR: δ 8.06 (2Η, d, J = 8Hz), 7.65 (2H, m), 7.47-7.25 (3H, m), 7.19 (2H, d, J = 8Hz), 7.13 (1 H, d, J = 2Hz), 7.04 (1 H, dd, J = 8 A 2Hz), 6.70 (1 H, d, J = 8Hz), 4.85-4.65 (4H, m), 4.21 (2H, s), 2.29 (3H, s), 1.78 (3H, s) 〇 謇 次 锎 1 8 (71) 4- (2- (N -Cyclopropylmethylbenzenesulfonamido) -4-methylphenoxymethyl] benzoic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) 120 3933 1 523506 A7 B7 V. Invention Instructions (121)

C〇〇H ΛC〇〇H Λ

T L C : R f 0·40 (氯仿：甲醇：乙酸=100:5:1); NMR (CD^COCD^) ：δ7.99(2Η, d, J=8.0Hz), 7.68 (2H, m), 7.26-7.57 (5H, m), 7.15 (2H, m), 6.96 (1H, d, J=8.8Hz), 4.93 (2H, brs), 3.52 (2H, brd, J=7.0Hz), 2.28 (3H, s), 0.90 (1H, m), 0.35 (2H, m), 0.06 (2H, m)〇 管 _ 例 1 8 (72) 4-[2-(N-異丙基丙磺釀胺基）-5-甲基苯氧甲基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)TLC: R f 0 · 40 (chloroform: methanol: acetic acid = 100: 5: 1); NMR (CD ^ COCD ^): δ7.99 (2Η, d, J = 8.0Hz), 7.68 (2H, m), 7.26-7.57 (5H, m), 7.15 (2H, m), 6.96 (1H, d, J = 8.8Hz), 4.93 (2H, brs), 3.52 (2H, brd, J = 7.0Hz), 2.28 (3H , s), 0.90 (1H, m), 0.35 (2H, m), 0.06 (2H, m). Tube_ Example 1 8 (72) 4- [2- (N-isopropylpropanesulfonamide) -5-methylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 T L C ： R f 0.24 (氯仿：甲醇=19:1); NM R ： δ 8.1 4 (2Η, d, J=8.2Hz), 7.57 (2H, d, J=8.2Hz), 7.16 (1 H, m), 6.82 (2H, m), 5.13 (2H, s), 4.33 (1H, m), 2.97 (2H, m), 2.36 (3H, s), 1.79 (2H, m), 1.23 (3H, d, J=6.6Hz), 1.09 (3H, d, J=6.6Hz), 0.85 (3H, t, J=7.4Hz)〇 謇嫵例1 8 ( 7 m 4-[2-(N-異丙基戊磺醢胺基）-5-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 121 3933 1 523506 A7 B7 五、發明説明（12会TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.24 (chloroform: methanol = 19: 1); NM R: δ 8.1 4 (2Η, d, J = 8.2Hz), 7.57 (2H, d, J = 8.2Hz), 7.16 (1 H, m), 6.82 (2H, m), 5.13 (2H, s), 4.33 (1H, m), 2.97 (2H, m), 2.36 (3H, s), 1.79 (2H , m), 1.23 (3H, d, J = 6.6Hz), 1.09 (3H, d, J = 6.6Hz), 0.85 (3H, t, J = 7.4Hz). Example 1 8 (7 m 4- [2- (N-Isopropylpentylsulfonamido) -5-methylphenoxymethyl] benzoic acid The paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 121 3933 1 523506 A7 B7 V. Description of Invention (12 sessions

TLC : R f 0.26 (氯仿：甲醇=19:1); NMR ： 5 8.15 (2H,d1J=8.0Hz), 7.56 (2H, d, J=8.0Hz), 7.14 (1H, m),6.81 (2H, m), 5.12 (2H, s), 4.32 (1H, m), 2.97 (2H, m), 2.36 (3H, s), 1.77 (2H, m), 1.24 (3H, d, J=6.6Hz), 1.16 (4H, m), 1.09 (3H, d, J=6.6Hz), 1.12 (3H, d, J=6.6Hz), 0.83 (3H, t, J=6.4Hz)〇 奮施例1 8 (7U 4-[2-(H-苄基甲磺醮胺基）-5-甲基苯氧甲基]苯甲酸 认、〇&gt;TLC: R f 0.26 (chloroform: methanol = 19: 1); NMR: 5 8.15 (2H, d1J = 8.0Hz), 7.56 (2H, d, J = 8.0Hz), 7.14 (1H, m), 6.81 (2H , m), 5.12 (2H, s), 4.32 (1H, m), 2.97 (2H, m), 2.36 (3H, s), 1.77 (2H, m), 1.24 (3H, d, J = 6.6Hz) , 1.16 (4H, m), 1.09 (3H, d, J = 6.6Hz), 1.12 (3H, d, J = 6.6Hz), 0.83 (3H, t, J = 6.4Hz). Example 1 8 ( 7U 4- [2- (H-benzylmethanesulfonamido) -5-methylphenoxymethyl] benzoic acid, 〇 &gt;

COOH (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標隼局員工消費合作社印製 〇2S、、 T L C ： R f 0.39 (氯仿：甲醇=19:1); NM R ： δ 8.17 (2Η, d, J=8.0Hz), 7.53 (2H, d, J=8.0Hz), 7.25 (5H, s), 6.98 (1 H, m), 6·77 (2H, m), 5.17 (2H, s)，4.70 (2H，bs), 2.89 (3H，s)，2.30 (3H, s)。 窨 Jfe 例 1 8 ( 7 5 ) 、 4-[2-(H-苄基丙磺醢胺基）-5-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 122 3933 1 523506 A7 B7 五、發明説明（12沒COOH (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs, 02C, TLC: R f 0.39 (chloroform: methanol = 19: 1); NM R: δ 8.17 ( 2Η, d, J = 8.0Hz), 7.53 (2H, d, J = 8.0Hz), 7.25 (5H, s), 6.98 (1 H, m), 6.77 (2H, m), 5.17 (2H, s), 4.70 (2H, bs), 2.89 (3H, s), 2.30 (3H, s).窨 Jfe Example 1 8 (7 5), 4- [2- (H-benzylpropanesulfonamido) -5-methylphenoxymethyl] benzoic acid The paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 122 3933 1 523506 A7 B7 V. Description of the invention (12

COOH 丁 L C : R f 〇.40 (氯仿：甲醇=19:1); ' NM R ： δ 8.1 7 (2Η, d, J=8.2Hz), 7.55 (2H, d, J=8.2Hz), 7.23 (5H, s), 6.98 (1 H, m), 6.78 (2H, m), 5.16 (2H, s), 4.77 (2H, bs), 2.95 (2H, m), 2.29 (3H, s), 1.81 (2H，m), 0.85 (3H, t，J=7.6Hz)。 奮胞例1 8 (7fi) 4 - [2-(N-異丙基環戊基磺釀胺基卜5-甲基苯氧甲基]苯甲 酸COOH but LC: R f 〇40 (chloroform: methanol = 19: 1); 'NM R: δ 8.1 7 (2Η, d, J = 8.2Hz), 7.55 (2H, d, J = 8.2Hz), 7.23 (5H, s), 6.98 (1 H, m), 6.78 (2H, m), 5.16 (2H, s), 4.77 (2H, bs), 2.95 (2H, m), 2.29 (3H, s), 1.81 (2H, m), 0.85 (3H, t, J = 7.6Hz). Example 1 (7fi) 4-[2- (N-Isopropylcyclopentylsulfonylaminomethyl 5-methylphenoxymethyl) benzoic acid

COOH TLC ： R f 0.38 (氯仿••甲醇··乙酸=1 〇 〇 : 5 : 1); 經濟部中央標隼局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) NM R ： δ 8.15 (2Η, d, J=8.0Hz), 7.59 (2H, d, J=8.0Hz), 7.14 (1 H, d, J=8.6Hz), 6.81 (2H, m), 5.12 (2H, s), 4.35 (1H，t峯，J=6.6Hz)，3.51 (1H, m)，2.36 (3H, s), 1.85-2.15 (3H,m), 1.61-1.85 (3H, m), 1.34-1.61 (2H, m)^ 1.22 (3H, d, J=6.6Hz), 1.08 (3H,d, J=6.6Hz)〇 奮 _ 例 1 8 (77) 4-[2-(N-異丙基乙磺醢胺基）-4-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 123 3933 1 523506 A7 B7 五、發明説明（1 2COOH TLC: R f 0.38 (chloroform •• methanol · • acetic acid = 1 00: 5: 1); printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) NM R : Δ 8.15 (2Η, d, J = 8.0Hz), 7.59 (2H, d, J = 8.0Hz), 7.14 (1 H, d, J = 8.6Hz), 6.81 (2H, m), 5.12 (2H, s), 4.35 (1H, t peak, J = 6.6Hz), 3.51 (1H, m), 2.36 (3H, s), 1.85-2.15 (3H, m), 1.61-1.85 (3H, m), 1.34- 1.61 (2H, m) ^ 1.22 (3H, d, J = 6.6Hz), 1.08 (3H, d, J = 6.6Hz) 〇fen_ Example 1 8 (77) 4- [2- (N-isopropyl Ethylsulfonamido) -4-methylphenoxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 123 3933 1 523506 A7 B7 V. Description of the invention (1 2

Me 〇2S、/Me 〇2S, /

C〇〇H TLC ： R f 0.23 (己烷：乙酸乙酯=1:1); NM R ： δ 8.1 5 (2H, d, J=8Hz), 7.53 (2H, d, J=8Hz), 7.21 (1 H, d, J=1.5Hz), 7.08 (1H, dd, J=8.5, 1.5Hz), 6.86 (1H, d, J=8.5Hz), 5.17 (2H, s), 3.46 (2H, d, J=7.5Hz), 2.97 (2H, q, J=7.5Hz), 2.30 (3H, s), 1.7-1 .5 (1H, m), 1.25 (3H, t, J=7.5Hz), 0.94-0.90 (6H, m)〇 奮施例1 8 ( 7 8 ) 4-[2-(N-異丙基丙磺醣胺基）-4-甲基苯氧甲基]苯甲酸C〇H TLC: R f 0.23 (hexane: ethyl acetate = 1: 1); NM R: δ 8.1 5 (2H, d, J = 8Hz), 7.53 (2H, d, J = 8Hz), 7.21 (1 H, d, J = 1.5Hz), 7.08 (1H, dd, J = 8.5, 1.5Hz), 6.86 (1H, d, J = 8.5Hz), 5.17 (2H, s), 3.46 (2H, d , J = 7.5Hz), 2.97 (2H, q, J = 7.5Hz), 2.30 (3H, s), 1.7-1 .5 (1H, m), 1.25 (3H, t, J = 7.5Hz), 0.94 -0.90 (6H, m) 〇 Example 1 8 (7 8) 4- [2- (N-isopropylpropanesulfonylamino) -4-methylphenoxymethyl] benzoic acid

Me 〇2S、^\Me 〇2S, ^ \

C〇〇H (請先閲讀背面之注意事項再填寫本頁) 丁 L C : R f 0.27 (己烷：乙酸乙酯=1:1); NM R ： δ 8.1 5 (2H, d, J=8Hz), 7.53 (2H, d, J=8Hz), 7.20 (1 H, d, J=0.5Hz), 7.08 經濟部中央標準局員工消費合作社印製 (1H, dd, J=8, 0.5Hz), 6.86 (1H, d, J=8Hz), 5.17 (2H, s), 3.44 (2H, d, J=7Hz), 2.94-2.86 (2H, m), 2.30 (3H, s), 1.9-1.6 (3H, m), 1 .0-0.9(6H, m), 0.85 (3H, t, J=7Hz)〇 富濂例18 (79) 4-[2-(N-異丁基丁磺醢胺基）-4-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 124 3933 1 523506 A7 B7 五、發明説明（125)C〇〇H (Please read the precautions on the back before filling this page) DLC: R f 0.27 (hexane: ethyl acetate = 1: 1); NM R: δ 8.1 5 (2H, d, J = 8Hz ), 7.53 (2H, d, J = 8Hz), 7.20 (1 H, d, J = 0.5Hz), 7.08 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (1H, dd, J = 8, 0.5Hz), 6.86 (1H, d, J = 8Hz), 5.17 (2H, s), 3.44 (2H, d, J = 7Hz), 2.94-2.86 (2H, m), 2.30 (3H, s), 1.9-1.6 (3H , m), 1.0-0.9 (6H, m), 0.85 (3H, t, J = 7Hz). Rich example 18 (79) 4- [2- (N-isobutylbutylsulfonamido) -4-Methylphenoxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) 124 3933 1 523506 A7 B7 V. Description of the invention (125)

C〇〇HC〇〇H

Me T L C : R f 0.37 (己烷：乙酸乙酯=1:1); NM R ： δ 8.15 (2H, d, J=8Hz), 7.53 (2H, d, J=8Hz), 7.20 (1 H, d, J=0.5Hz), 7.08 (1 H, dd, J-8.5, 0.5Hz), 6.86 (1 H, d, J=8.5Hz), 5.16 (2H, s), 3.45 (2H, d, J=7Hz), 2.97-2.89 (2H, m), 2.30 (3H, s), 1.8-1.5 (3H , m), 1.3-1.1 (2H, m), 1.0-0.9(6H, m), 0.79 (3H, t, J=7Hz)〇 奮淪锎1 8 ( 8 0 ) 4-[2-(N-異丁基丙磺釀胺基）_5-甲基苯氧甲基]苯甲酸Me TLC: R f 0.37 (hexane: ethyl acetate = 1: 1); NM R: δ 8.15 (2H, d, J = 8Hz), 7.53 (2H, d, J = 8Hz), 7.20 (1 H, d, J = 0.5Hz), 7.08 (1 H, dd, J-8.5, 0.5Hz), 6.86 (1 H, d, J = 8.5Hz), 5.16 (2H, s), 3.45 (2H, d, J = 7Hz), 2.97-2.89 (2H, m), 2.30 (3H, s), 1.8-1.5 (3H, m), 1.3-1.1 (2H, m), 1.0-0.9 (6H, m), 0.79 (3H , t, J = 7Hz) 〇Fen 锎 1 8 (8 0) 4- [2- (N-isobutylpropanesulfonylamino) _5-methylphenoxymethyl] benzoic acid

Me (請先閱讀背面之注意事項再填寫本頁) ^γ〇〇〇Η 〇2S、^\ 丁 L C : R f 0.25 (氯仿：甲醇=20:1); 經濟部中央標準局員工消費合作社印製 NM R : δ 8·1 6 (2H, d, J=8.4Hz), 7_53 (2H，d, J=8.4Hz), 7.28 (1 H, m), 6·82 (2H, m), 5.18 (2H, s), 3.41 (2H, d, J=7.0Hz) ,2.89 (2H, m), 2.35 (3H, s), 1.78 (2H, m), 1.60 (1H, m), 0.90 (6H, d, J=7.0Hz), 0.84 (3ΗΛ 7.6Hz)。 奮施例1 8 ( 8 1) 4-[2-[N-(丙-2-烯基）丙磺醢胺基卜5-甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 125 3933 1 523506 A7 B7 五、發明説明（126)Me (Please read the precautions on the back before filling in this page) ^ γ〇〇〇〇 〇2S, ^ \ Ding LC: R f 0.25 (chloroform: methanol = 20: 1); printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs NM R: δ 8 · 1 6 (2H, d, J = 8.4Hz), 7_53 (2H, d, J = 8.4Hz), 7.28 (1 H, m), 6.82 (2H, m), 5.18 (2H, s), 3.41 (2H, d, J = 7.0Hz), 2.89 (2H, m), 2.35 (3H, s), 1.78 (2H, m), 1.60 (1H, m), 0.90 (6H, d, J = 7.0Hz), 0.84 (3ΗΛ 7.6Hz). Fenshi Example 1 8 (8 1) 4- [2- [N- (Prop-2-enyl) propanesulfonylaminomethyl 5-methylphenoxymethyl] benzoic acid The paper size applies to Chinese national standards ( CNS) A4 specification (210X297 mm) 125 3933 1 523506 A7 B7 V. Description of the invention (126)

C〇〇HC〇〇H

N 〇2S\/\ TLC ： R f 0.23 (氛仿：甲醇= 20:1); NM R ： δ 8.1 6 (2H, d, J=8.4Hz), 7.56 (2H, d, J=8.4Hz), 7.21 (1 H, m), 6.90 (2H, m), 5.80 (1H, m), 5.17 (2H, s), 5.07 (2H, m), 4.21 (2H, d, J=6.2Hz), 2.94 (2H, m), 2.34 (3H, s), 1.81 (2H, m), 0.86 (3H, t, J=7.4Hz)〇 g 施例 18 (82) 4 - [2-[N-(2-甲基丙-2-烯基）磺醢胺基]-5-甲基苯氧甲基] 笨甲酸 (請先閱讀背面之注意事項再填寫本頁)N 〇2S \ / \ TLC: R f 0.23 (Diffuse: Methanol = 20: 1); NM R: δ 8.1 6 (2H, d, J = 8.4Hz), 7.56 (2H, d, J = 8.4Hz) , 7.21 (1 H, m), 6.90 (2H, m), 5.80 (1H, m), 5.17 (2H, s), 5.07 (2H, m), 4.21 (2H, d, J = 6.2Hz), 2.94 (2H, m), 2.34 (3H, s), 1.81 (2H, m), 0.86 (3H, t, J = 7.4Hz) 〇g Example 18 (82) 4-[2- [N- (2- Methylprop-2-enyl) sulfonamido] -5-methylphenoxymethyl] stearic acid (Please read the precautions on the back before filling this page)

Me 〇2S^&lt;Me 〇2S ^ &lt;

COOH 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.28 (氯仿：甲醇= 20:1); NM R ： δ 8.16 (2H, d, J=8.2Hz), 7.54 (2H, d, J=8.2Hz), 7.23 (1 H, m), 6.78 (2H, m), 5.17 (2H, s), 4.75 (2H, s), 4.18 (2H, s), 2.88 (2H, m), 2.34 (3H, s), 1.79 (2H, m), 1.78 (3H, s), 0.85 (3H, t, J=7.6Hz)。 奮施例1 8 ( 8 ” ( 4-[2-(N-異丁基苯磺醢胺基）-4-氯笨氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 126 3933 1 523506 A7 B7 五、發明説明（1 27)COOH Printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.28 (chloroform: methanol = 20: 1); NM R: δ 8.16 (2H, d, J = 8.2Hz), 7.54 (2H, d, J = 8.2Hz), 7.23 (1 H, m), 6.78 (2H, m), 5.17 (2H, s), 4.75 (2H, s), 4.18 (2H, s), 2.88 (2H, m), 2.34 (3H , s), 1.79 (2H, m), 1.78 (3H, s), 0.85 (3H, t, J = 7.6Hz). Fen Shi Example 1 8 (8 ”(4- [2- (N-isobutylbenzenesulfonamido) -4-chlorobenzyloxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 specifications ( 210X297 mm) 126 3933 1 523506 A7 B7 V. Description of the invention (1 27)

CI 〇2S^^CI 〇2S ^^

C〇〇H T L C ： R f 0.29 (氯仿：甲醇=19:1); NM R ： δ 8.06 (2H, d, J=8.0Hz), 7.64 (2H, d, J=8.0Hz), 7.20-7.40 (7H, m), 6.78 (1H, m), 4.80 (2H, bs), 3.40 (2H, d, J=7.0Hz), 1.61 (1H, m), 0.90 (6H, d, J=7.0Hz)〇 實施例1 8 ( 8 4 ) 4-[2-(»1_丙基丙磺醸胺基）-5-甲基苯氧甲基]苯甲酸C〇HTLC: R f 0.29 (chloroform: methanol = 19: 1); NM R: δ 8.06 (2H, d, J = 8.0Hz), 7.64 (2H, d, J = 8.0Hz), 7.20-7.40 ( 7H, m), 6.78 (1H, m), 4.80 (2H, bs), 3.40 (2H, d, J = 7.0Hz), 1.61 (1H, m), 0.90 (6H, d, J = 7.0Hz). Example 1 8 (8 4) 4- [2-(»1-propanesulfonamido) -5-methylphenoxymethyl] benzoic acid

C〇〇H (請先閲讀背面之注意事項再填寫本頁) Ν〆 經濟部中央標準局員工消費合作社印裝 Τ L C ： R f 0.52 (氯仿：甲醇=9:1); NMR ： 58.17 (2H, d, J=8.4Hz), 7.55 (2H,d, J=8.4Hz), 7.25 (1H, d, J=8.2Hz), 6.9- 6.8 (2H, m), 5.17 (2H, s), 3.56 (2H, t, J=7.4Hz), 3.0-2.8 (2H, m), 2.35 (3H, s), 1.9- 1.7 (2H, m), 1.6-1.4 (2H, m), 0.89 (3H, t, J=7.2Hz), 0.84 (3H, t, J=7.4Hz)〇 窗淪例18 (只、 4-[2-(N-異丁基己磺醢胺基）-4-甲基苯氧甲基]笨甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 127 3933 1 523506 A7 B7 五、發明説明（12$C〇〇H (Please read the notes on the back before filling out this page) Ν 印 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs LC: R f 0.52 (chloroform: methanol = 9: 1); NMR: 58.17 (2H , d, J = 8.4Hz), 7.55 (2H, d, J = 8.4Hz), 7.25 (1H, d, J = 8.2Hz), 6.9- 6.8 (2H, m), 5.17 (2H, s), 3.56 (2H, t, J = 7.4Hz), 3.0-2.8 (2H, m), 2.35 (3H, s), 1.9- 1.7 (2H, m), 1.6-1.4 (2H, m), 0.89 (3H, t , J = 7.2Hz), 0.84 (3H, t, J = 7.4Hz). Example 18 (only, 4- [2- (N-isobutylhexylsulfonamido) -4-methylphenoxy) Methyl] stearic acid This paper is sized for Chinese National Standard (CNS) A4 (210X 297 mm) 127 3933 1 523506 A7 B7 V. Description of the invention (12 $

C〇〇HC〇〇H

Me Τ L C : R f 0.49 (氯仿··甲醇=：9 ·· 1 ); NM R ： δ 8.16 (2H, d, J=8.4Hz), 7.53 (2H, d, J=8.4Hz), 7.21 (1 H, d, J=2.0Hz), 7.09 (1H, dd, J=2.0, 8.4Hz), 6.87 (1H, d, J=8.4Hz), 5.16 (2H, s), 3.45 (2H, d, J=7.0Hz), 3.0-2.8 (2H, m), 2.30 (3H, s), 1.8-1.5 (3H, m), 1.3-1.0 (6H, m), 1.0-0.8 (6H, m), 0.83 (3H, t, J=7.0Hz)〇 奮淪例1 8 4-[2-(N-異丁基戊磺醢胺基）-4-甲基苯氧甲基]苯甲酸Me Τ LC: R f 0.49 (chloroform ·· methanol =: 9 ·· 1); NM R: δ 8.16 (2H, d, J = 8.4Hz), 7.53 (2H, d, J = 8.4Hz), 7.21 ( 1 H, d, J = 2.0Hz), 7.09 (1H, dd, J = 2.0, 8.4Hz), 6.87 (1H, d, J = 8.4Hz), 5.16 (2H, s), 3.45 (2H, d, J = 7.0Hz), 3.0-2.8 (2H, m), 2.30 (3H, s), 1.8-1.5 (3H, m), 1.3-1.0 (6H, m), 1.0-0.8 (6H, m), 0.83 (3H, t, J = 7.0 Hz) Example 1 8 4- [2- (N-Isobutylpentylsulfonamido) -4-methylphenoxymethyl] benzoic acid

C〇〇HC〇〇H

Me TLC ： R f 0.38 (氯仿··甲醇：乙酸=100:5:1); NM R ： δ 8.16 (2H, d, J=8.4Hz), 7.53 (2H, d, J=8.4Hz), 7.21 (1 H, d, J=2.2Hz), 經濟部中央標準局g〈工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 7.09 (1 H, dd, J=2.2, 8.6Hz), 6.87 (1 H, d, J=8.6Hz), 5.16 (2H, s), 3.45 (2H, d, J=7.2H2), 2.91 (2H, m), 2.30 (3H, s), 1.74 (2H, m), 1.60 (1 H, m), 1.17 (4H, m), 0.92 (6H, m), 0.82 (3H, m)〇 奮施例18 (87) 4-[2-[H-(丙-2-烯基）丙磺醢胺基）-5-三氟甲基苯氧甲基] 苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 128 3933 1 523506 A7 B7 五、發明説明（12^Me TLC: R f 0.38 (chloroform · methanol: acetic acid = 100: 5: 1); NM R: δ 8.16 (2H, d, J = 8.4Hz), 7.53 (2H, d, J = 8.4Hz), 7.21 (1 H, d, J = 2.2Hz), Central Standards Bureau of the Ministry of Economic Affairs g <Printed by Industrial and Consumer Cooperatives (please read the precautions on the back before filling this page) 7.09 (1 H, dd, J = 2.2, 8.6Hz ), 6.87 (1 H, d, J = 8.6Hz), 5.16 (2H, s), 3.45 (2H, d, J = 7.2H2), 2.91 (2H, m), 2.30 (3H, s), 1.74 ( 2H, m), 1.60 (1 H, m), 1.17 (4H, m), 0.92 (6H, m), 0.82 (3H, m). Example 18 (87) 4- [2- [H- ( Prop-2-enyl) Propanesulfonylamino) -5-trifluoromethylphenoxymethyl] Benzoic acid This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 128 3933 1 523506 A7 B7 V. Description of the invention (12 ^

C〇〇HC〇〇H

XI °2S^\ 丁 L C : R f 0·33 (己烷··乙酸乙酯=1:1); NMR (200MHz, CDCI3+1 滴 CD?〇D) ： δ 8.15-8.11 (2H, m), 7.54- 7.44(3H, m), 7.30-7.24 (2H, m), 5.88-5.68 (1H, m), 5.20 (2H, s), 5.12-5.10 (1 H, m), 5.04-5.03 (1H, m), 4.21 (2H, d, J=6.5Hz), 2.95-2.87 (2H, m), 1.8-1.7 (1H, m), 0.84 (3H, t, J=7.5 Hz)。 奮 _ 例 1 8 (88) 4-[2-[N-(2-甲基丙-2-烯基）丙磺釀胺基]-5-三氟甲基苯 氧甲基]苯甲酸XI ° 2S ^ \ DLC: R f 0 · 33 (hexane · ethyl acetate = 1: 1); NMR (200MHz, CDCI3 + 1 drop CD? 〇D): δ 8.15-8.11 (2H, m) , 7.54- 7.44 (3H, m), 7.30-7.24 (2H, m), 5.88-5.68 (1H, m), 5.20 (2H, s), 5.12-5.10 (1 H, m), 5.04-5.03 (1H , m), 4.21 (2H, d, J = 6.5Hz), 2.95-2.87 (2H, m), 1.8-1.7 (1H, m), 0.84 (3H, t, J = 7.5 Hz). Fen _ Example 1 8 (88) 4- [2- [N- (2-methylprop-2-enyl) propanesulfonylamino] -5-trifluoromethylphenoxymethyl] benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

F3C 經濟部中央標準局員工消費合作社印製 TLC ： R f 0.41 (己烷：乙酸乙酯=1:1); NM R ： δ 8.30 (2Η, d, J=8Hz), 7.71 -7.67 (2H, m), 7.62-7.56 (1 H, m), 7.40-7.35 (2H, m), 5.34 (2H, s), 4.89-4.85 (2H, m), 5.34 (2H, s), 4.89-4.85 (2H, m), 4.31 (2H, s), 3.07-2.99 (2H, m), 2.0-1.8 (2H, m), 1.8 7 (3H, s), 1.00-0.93 (3H, m)〇 窖施例18 (89) 4-[2-(N-丙基-2-呋喃磺醢胺基）-5-三氟甲基苯氧甲基]桂 皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 129 3 93 3 1 523506 A7 B7 經濟部中央標隼局員工消費合作社印製 五、發明説明（13&amp; N〆F3C TLC printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.41 (hexane: ethyl acetate = 1: 1); NM R: δ 8.30 (2Η, d, J = 8Hz), 7.71 -7.67 (2H, m), 7.62-7.56 (1 H, m), 7.40-7.35 (2H, m), 5.34 (2H, s), 4.89-4.85 (2H, m), 5.34 (2H, s), 4.89-4.85 (2H , m), 4.31 (2H, s), 3.07-2.99 (2H, m), 2.0-1.8 (2H, m), 1.8 7 (3H, s), 1.00-0.93 (3H, m). Example 18 (89) 4- [2- (N-propyl-2-furansulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid The paper size applies to Chinese National Standard (CNS) A4 specification (210 X 297 mm) 129 3 93 3 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs V. Invention Description (13 &amp; N〆

〇2S〇2S

丁 L C : R f 0.38 (己烷：乙酸乙酯=1:1); NM R ： δ 7.81 (1 H, d, J=16Hz), 7.59 (2H, d, J=8Hz), 7.42-7.37 (3H, m), 7.28- 7.24 (2H, m), 7.18 (1H, d, J=1.5Hz), 6.85 (1H, dd, J=3, 1Hz), 6.49 (1H, d, J=16Hz), 6.35 (1 H, dd, J=3, 2Hz), 5.03 (2H, s), 3.71 - 3.64 (2H, m), 1.6-1.4 (2H, m), 0.88 (3H, t，J=7Hz)。 簠施例】8 ( Q 0 ) 4-[2-(N-丙基-丙磺醏胺基）-5-三氟甲基苯氧甲基]苯甲酸DLC: R f 0.38 (hexane: ethyl acetate = 1: 1); NM R: δ 7.81 (1 H, d, J = 16Hz), 7.59 (2H, d, J = 8Hz), 7.42-7.37 ( 3H, m), 7.28- 7.24 (2H, m), 7.18 (1H, d, J = 1.5Hz), 6.85 (1H, dd, J = 3, 1Hz), 6.49 (1H, d, J = 16Hz), 6.35 (1 H, dd, J = 3, 2Hz), 5.03 (2H, s), 3.71-3.64 (2H, m), 1.6-1.4 (2H, m), 0.88 (3H, t, J = 7Hz). Example] 8 (Q 0) 4- [2- (N-propyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid

XX hr (請先閱讀背面之注意事項再填寫本頁)XX hr (Please read the notes on the back before filling this page)

C〇〇H 〇2S\/\ T L C ： R f 0.40 (氯仿：甲醇=9:1); NMR ： 5 8.17 (2H,d,J=8.2Hz), 7.56 (2H, d, J=8.2Hz), 7.49 (1H, m), 7.27 (2H, m), 5.22 (2H, s), 3.58 (2H, m), 2.91 (2H, m), 1.79 (2H, m), 1.45 (2H, m), 0.89 (3H, t, J=7.4Hz), 0.85 (3H, t, J=7.6Hz)〇 g 施例 1 8 (Q1、 4- [2- (N-異丁基-丙磺醢胺基 酸 )-5-三氟甲基苯氧甲基]苯甲 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 130 3933 1C〇H 〇2S \ / \ TLC: R f 0.40 (chloroform: methanol = 9: 1); NMR: 5 8.17 (2H, d, J = 8.2Hz), 7.56 (2H, d, J = 8.2Hz) , 7.49 (1H, m), 7.27 (2H, m), 5.22 (2H, s), 3.58 (2H, m), 2.91 (2H, m), 1.79 (2H, m), 1.45 (2H, m), 0.89 (3H, t, J = 7.4Hz), 0.85 (3H, t, J = 7.6Hz) 0 g Example 1 8 (Q1, 4- [2- (N-isobutyl-propanesulfonamide) ) -5-Trifluoromethylphenoxymethyl] Benzene This paper is sized for China National Standard (CNS) A4 (210X 297 mm) 130 3933 1

523506 A7 B7 五、發明説明（1 3523506 A7 B7 V. Description of the invention (1 3

COOH 丁 L C : R f 0.45 (氯仿：甲醇=9:1); NM R ： δ 8.1 8 (2Η, d, J=8.2Hz), 7.56 (2H, d, J=8.2Hz), 7.51 (1 H, m), 7.28 (2H, m), 5.23 (2H, s), 3.45 (2H, d, J=7.4Hz), 2.89 (2H, m), 1.75 (2H, m), 1.58 (1H, m), 0.90 (6H, d，J=6.8Hz)，0.84 (3H，t, J=7.4Hz)。 奮 _ 例 1 8 ( 9 2 ) 4-[2-(N-丙基-2-呋喃磺醢胺基）-5-甲基苯氧甲基]苯甲酸COOH butyl LC: R f 0.45 (chloroform: methanol = 9: 1); NM R: δ 8.1 8 (2Η, d, J = 8.2Hz), 7.56 (2H, d, J = 8.2Hz), 7.51 (1 H , m), 7.28 (2H, m), 5.23 (2H, s), 3.45 (2H, d, J = 7.4Hz), 2.89 (2H, m), 1.75 (2H, m), 1.58 (1H, m) , 0.90 (6H, d, J = 6.8Hz), 0.84 (3H, t, J = 7.4Hz). Fen _ Example 1 8 (9 2) 4- [2- (N-propyl-2-furansulfonamido) -5-methylphenoxymethyl] benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁) h3c^y〇 n〆o2s.COOH (Please read the notes on the back before filling this page) h3c ^ y〇 n〆o2s.

T L C : R f 〇_38 (己烷：乙酸乙酯=1:1); 經濟部中央標準局員工消費合作社印製 NMR ： 58.13 (2H, d, J=8Hz), 7.44 (2H, d, J=8Hz), 7.25 (1H, m), 7.12 (1H, d, J=8Hz), 6.83-6.73 (3H, m), 6.33-6.30 (1H, m), 5.01 (2H, s), 3.7-3.6 (2H, m), 2.33 (3H，s), 1.52 (2H, q，J=7Hz), 0.90 (3H, t, J=7Hz)。 g _ 例 1 8 ( 9 3) 4-[2-(N-異丁基-2-呋喃磺醢胺基）-5-甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 131 3933 1 523506 A7 B7 五、發明説明（1 3这TLC: R f 〇_38 (hexane: ethyl acetate = 1: 1); NMR printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: 58.13 (2H, d, J = 8Hz), 7.44 (2H, d, J = 8Hz), 7.25 (1H, m), 7.12 (1H, d, J = 8Hz), 6.83-6.73 (3H, m), 6.33-6.30 (1H, m), 5.01 (2H, s), 3.7-3.6 (2H, m), 2.33 (3H, s), 1.52 (2H, q, J = 7Hz), 0.90 (3H, t, J = 7Hz). g _ Example 1 8 (9 3) 4- [2- (N-isobutyl-2-furansulfonamido) -5-methylphenoxymethyl] benzoic acid The paper size is applicable to Chinese national standards (CNS ) A4 specification (210X297 mm) 131 3933 1 523506 A7 B7 V. Description of the invention (1 3this

MeMe

OC j〇rOC j〇r

C〇〇H 〇2S\C〇〇H 〇2S \

T L C ： R f 0.41 (己烷··乙酸乙酯=1 : 1 ); NMR ： 58.13 (2H, d, J=8Hz), 7.44 (2H, d, J=8Hz), 7.25 (1H, m), 7.15 (1H, d, J=8Hz), 6.80-6.71 (3H, m), 6.31 (1 H, m), 5.0 (2H, m), 3.53 (2H, d, J=7Hz), 1.75-1.60(1H, m), 0.91 (6H, t, J=7Hz)〇 奮 _ 俐 1 8 (Q4)4-[2-(H-異丁基-2-呋喃磺醢胺基）-5-三氟甲基笨氧甲基] (請先閱讀背面之注意事項再填寫本頁) 桂皮酸TLC: R f 0.41 (hexane · ethyl acetate = 1: 1); NMR: 58.13 (2H, d, J = 8Hz), 7.44 (2H, d, J = 8Hz), 7.25 (1H, m), 7.15 (1H, d, J = 8Hz), 6.80-6.71 (3H, m), 6.31 (1 H, m), 5.0 (2H, m), 3.53 (2H, d, J = 7Hz), 1.75-1.60 ( 1H, m), 0.91 (6H, t, J = 7Hz). Fen_Li 1 8 (Q4) 4- [2- (H-isobutyl-2-furansulfonamido) -5-trifluoromethyl Benzyloxymethyl] (Please read the notes on the back before filling out this page) Cinnamate

經濟部中央標隼局員工消費合作社印製Printed by the Staff Consumer Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs

COOH T L C : R f 0.44 (己烷：乙酸乙酯=1:1); NMR ： 5 7.81 (1H, d, J=16Hz), 7.60 (2H,d, J=8Hz), 7.41-7.37 (3H, m), 7.27-7.22 (2H, m), 7.17 (1H, m), 6.83 (1H, dd, J=3.5, 1.5Hz), 6.49 (1H, d, J=16Hz), 6.35 (1 H, dd, J=3.5, 1.5Hz), 5.02 (2H, s), 3.53 (2H, d, J=7.5 Hz), 1.74-1.50 (1 H, m),0.90 (6H,d, J=6.5Hz)。 g 锎 1 8 f 9 ;n 4-[2-(H-丙基-苯磺酿胺基）-5-甲基苯氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 132 3933 1 523506 A7 B7 五、發明説明（1 33)COOH TLC: R f 0.44 (hexane: ethyl acetate = 1: 1); NMR: 5 7.81 (1H, d, J = 16Hz), 7.60 (2H, d, J = 8Hz), 7.41-7.37 (3H, m), 7.27-7.22 (2H, m), 7.17 (1H, m), 6.83 (1H, dd, J = 3.5, 1.5Hz), 6.49 (1H, d, J = 16Hz), 6.35 (1 H, dd , J = 3.5, 1.5Hz), 5.02 (2H, s), 3.53 (2H, d, J = 7.5 Hz), 1.74-1.50 (1 H, m), 0.90 (6H, d, J = 6.5Hz). g 锎 1 8 f 9; n 4- [2- (H-propyl-benzenesulfonylamino) -5-methylphenoxymethyl] cinnamic acid The paper size applies to Chinese National Standard (CNS) A4 specifications ( 210X297 mm) 132 3933 1 523506 A7 B7 V. Description of the invention (1 33)

02S T L C : R f 0.33 (氯仿：甲醇·•乙酸=100:5:1); NM R ：δ 7.79 (1 H, d, J=16.0Hz), 7.67 (2H, m), 7.51 (2H, d, J=8.0Hz), 7.24-7.43 (3H, m), 7.17 (2H, d, J=8.0Hz), 7.15 (1H, d, J=8.0Hz), 6.78 (1H, m), 6.68 (1H, m), 6.47 (1 H, d, J=16.0Hz), 4.79 (2H, brs), 3.55 (2H, m), 2.34 (3H, s), 1.47 (2H, m)，0.87 (3H,t, J=7.2Hz)。 奮淪例1 8 (Qfn 4-[2-(H-異丁基苯磺醢胺基）-5 -甲基苯氧甲基]桂皮酸02S TLC: R f 0.33 (chloroform: methanol · acetic acid = 100: 5: 1); NM R: δ 7.79 (1 H, d, J = 16.0Hz), 7.67 (2H, m), 7.51 (2H, d , J = 8.0Hz), 7.24-7.43 (3H, m), 7.17 (2H, d, J = 8.0Hz), 7.15 (1H, d, J = 8.0Hz), 6.78 (1H, m), 6.68 (1H , m), 6.47 (1 H, d, J = 16.0Hz), 4.79 (2H, brs), 3.55 (2H, m), 2.34 (3H, s), 1.47 (2H, m), 0.87 (3H, t , J = 7.2Hz). Example 1 (Qfn 4- [2- (H-isobutylbenzenesulfonamido) -5 -methylphenoxymethyl] cinnamic acid

COOH T L C ： R f 0.37 (氯仿：甲醇：乙酸=100:5:1); 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) NMR ：δ7.79 (1H, d, J=16.0Hz), 7.63 (2H, m), 7.51 (2H, d, J=8.2Hz), 7.24-7.46 (3H, m), 7.18 (1H, d, J=7.8Hz), 7.16 (2H, d, J=8.2Hz), 6.78 (1H, m), 6.66 (1H, m), 6.48 (1 H, d, J=16.0Hz), 4.74 (2H, m), 3.41 (2H, m), 2.33 (3H, s), 1.61 (1 Ht m), 0·89 (6H, d，J=6.4Hz)。 、 奮淪例1 8 ( 97 ) 4-[2-(N-異丁基-丙磺醸胺基）-5-三氟甲基苯氧甲基]桂皮 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 133 3933 1COOH TLC: R f 0.37 (chloroform: methanol: acetic acid = 100: 5: 1); printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) NMR: δ7.79 (1H , d, J = 16.0Hz), 7.63 (2H, m), 7.51 (2H, d, J = 8.2Hz), 7.24-7.46 (3H, m), 7.18 (1H, d, J = 7.8Hz), 7.16 (2H, d, J = 8.2Hz), 6.78 (1H, m), 6.66 (1H, m), 6.48 (1 H, d, J = 16.0Hz), 4.74 (2H, m), 3.41 (2H, m ), 2.33 (3H, s), 1.61 (1 Ht m), 0 · 89 (6H, d, J = 6.4Hz). Example 1 8 (97) 4- [2- (N-isobutyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid The paper standard applies to Chinese national standard (CNS ) A4 size (210X297 mm) 133 3933 1

02S 523506 A7 B7 五、發明説明（1 34)02S 523506 A7 B7 V. Description of the invention (1 34)

COOH T L C : R f 0.36 (氯仿：甲酵：乙酸=100:5:1); NMR ： 5 7.80 (1H, d, J=16.0Hz), 7.62 (2H, d, J=8.4Hz), 7.44-7.56 (3H, m), 7.24-7.33 (2H, m), 6.50 (1 H, d, J=16.0Hz), 5.17 (2H, s), 3.44 (2H, d, J=7.4Hz), 2.87 (2H, m), 7.15 (2H, m), 1.55 (1H, m), 0.90 (6H, d, J=6.6Hz), 0.83 (3H, t, J=7.4H2)〇 奮餱锎1 8 (98) 4 - [2-(N-甲基-苯磺醢胺基）-5-三氟甲基苯氧甲基]桂皮酸COOH TLC: R f 0.36 (chloroform: formazan: acetic acid = 100: 5: 1); NMR: 5 7.80 (1H, d, J = 16.0Hz), 7.62 (2H, d, J = 8.4Hz), 7.44- 7.56 (3H, m), 7.24-7.33 (2H, m), 6.50 (1 H, d, J = 16.0Hz), 5.17 (2H, s), 3.44 (2H, d, J = 7.4Hz), 2.87 ( 2H, m), 7.15 (2H, m), 1.55 (1H, m), 0.90 (6H, d, J = 6.6Hz), 0.83 (3H, t, J = 7.4H2). Fendi 1 8 (98 ) 4-[2- (N-methyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

T L C ： R f 0.44 (氯仿：甲醇=9 ·· 1 ); 經濟部中央標準局員工消費合作社印繁 NM R ： δ 7.79 (1 H, d, J=16.2Hz), 7.7-7.6 (2H, m), 7.6-7.2 (7H, m), 7.2-7.1 (3H, m), 6.49 (1H, d, J=16.2Hz), 4·88 (2H，s), 3·23 (3H, s)。 奮 _ 例 1 8 ( 9 9 ) 、 4-[2-(N-丙基-苯磺酿胺基）-5-三氟甲基笨氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 134 39 33 1 523506 A7 B7 五、發明説明（1 35)TLC: R f 0.44 (chloroform: methanol = 9 ·· 1); NM R: δ 7.79 (1 H, d, J = 16.2 Hz), 7.7-7.6 (2H, m ), 7.6-7.2 (7H, m), 7.2-7.1 (3H, m), 6.49 (1H, d, J = 16.2Hz), 4.88 (2H, s), 3.23 (3H, s). Fen _ Example 1 8 (9 9), 4- [2- (N-propyl-benzenesulfonylamino) -5-trifluoromethylbenzyloxymethyl] cinnamic acid The paper size is applicable to the Chinese National Standard (CNS ) A4 specification (210X297 mm) 134 39 33 1 523506 A7 B7 V. Description of the invention (1 35)

F3CF3C

TLC ： R f 0.43 (氛仿：甲醇=9 : 1); NMR ：δ7.80 (1H, d, J=16.0Hz), 7.7-7.6 (2H, m), 7.6-7.1 (10H, m), 6.49 (1H, d, J=16.0Hz), 4.86 (2H, s), 3.57 (2H, t, J=7.2Hz), 1.6-1.3 (2H, m), 0.87 (3H, t, J=7.2Hz)〇 奮 _ 俐 1 8 (100) 4-[2-(N-異丁基-苯磺醸胺基）-5-三氟甲基苯氧甲基]桂皮 酸 (請先閱讀背面之注意事項再填寫本頁)TLC: R f 0.43 (methanol: 9 = 1); NMR: δ7.80 (1H, d, J = 16.0Hz), 7.7-7.6 (2H, m), 7.6-7.1 (10H, m), 6.49 (1H, d, J = 16.0Hz), 4.86 (2H, s), 3.57 (2H, t, J = 7.2Hz), 1.6-1.3 (2H, m), 0.87 (3H, t, J = 7.2Hz ) 〇fen_ Li 1 8 (100) 4- [2- (N-isobutyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid (Please read the precautions on the back first (Fill in this page again)

經濟部中央標準局員工消費合作社印製 TLC : R f 0.47 (氯仿：甲醇=9 : 1); NMR : δ7·80 (1H, d, J=16.0Hz), 7·7·7·1 (12H, m), 6.49 (1H, d, J=16OHz), 4.9-4.7 (2H, br), 3.42 (2H, d, J=7.6Hz)，1.7-1.5 (1H, m), 0·89 (6H, d, J=6.6Hz)。 奮施例1 8 (1 0 1 ) 4-[2-(N-異丙基-丙碣醸胺基）-5-甲基苯氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 135 3933 1 523506 A7 B7 五、發明説明（1 36)Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.47 (chloroform: methanol = 9: 1); NMR: δ7 · 80 (1H, d, J = 16.0Hz), 7 · 7 · 7 · 1 (12H , m), 6.49 (1H, d, J = 16OHz), 4.9-4.7 (2H, br), 3.42 (2H, d, J = 7.6Hz), 1.7-1.5 (1H, m), 0 · 89 (6H , d, J = 6.6Hz). Example 1 8 (1 0 1) 4- [2- (N-isopropyl-propanamido) -5-methylphenoxymethyl] cinnamic acid The paper size applies to Chinese National Standards (CNS) A4 specifications (210X297 mm) 135 3933 1 523506 A7 B7 V. Description of the invention (1 36)

COOH 〇2S、/^ 丁 L C : R f 0·44 (氯仿：甲醇=9 : 1); . NMR ：δ7.79 (1Η, d, J=16.0Hz), 7.53 (4H, m), 7.14 (1H, m), 6.80 (2H, m), 6.47 (1H,d, J=16.0Hz), 5.07 (2H, s), 4.31 (1H, m), 2.94 (2H, m), 1.79 (2H, m), 1.23 (3H, d, J=6.6Hz), 1.08 (3H, d, J=6.6Hz), 0.83 (3H, t, J=7.2Hz)〇 窗嬾锎1 8 (102) 4-[2-(H-乙基-苯磺醢胺基）-5-三氟甲基笨氧甲基]桂皮酸COOH 〇2S, butyl chloride: R f 0.44 (chloroform: methanol = 9: 1);. NMR: δ7.79 (1Η, d, J = 16.0Hz), 7.53 (4H, m), 7.14 ( 1H, m), 6.80 (2H, m), 6.47 (1H, d, J = 16.0Hz), 5.07 (2H, s), 4.31 (1H, m), 2.94 (2H, m), 1.79 (2H, m ), 1.23 (3H, d, J = 6.6Hz), 1.08 (3H, d, J = 6.6Hz), 0.83 (3H, t, J = 7.2Hz). Window laziness 1 8 (102) 4- (2 -(H-ethyl-benzenesulfonamido) -5-trifluoromethylbenzyloxymethyl] cinnamic acid

02S (請先閱讀背面之注意事項再填寫本頁)02S (Please read the notes on the back before filling this page)

COOH TLC : R f 0.37 (氯仿：甲醇=9:1); 經 濟 部 中 準 局 員 工 消 費 合 作 社 印 製 NMR : δ 7.79 (1H，d, J=16.0Hz), 7.60-7.71 (2H, m), 7.15-7.55 (10H, m), 6.49 (1H, d, J=16.0Hz), 4.89 (2H, s), 3·67 (2H, q, J=7.0Hz), 1.09 (3H, t, J=7.0Hz)。 窨）fe 俐 1 8 4-[2-(N-環丙基甲基-苯磺醸胺基）-5-三&lt;氟甲基苯氧甲基] 桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 136 3933 1 523506 A7 B7 五、發明説明（137)COOH TLC: R f 0.37 (chloroform: methanol = 9: 1); NMR printed by the Consumers' Cooperative of the China Central Standard Bureau of the Ministry of Economic Affairs: δ 7.79 (1H, d, J = 16.0Hz), 7.60-7.71 (2H, m), 7.15-7.55 (10H, m), 6.49 (1H, d, J = 16.0Hz), 4.89 (2H, s), 3.67 (2H, q, J = 7.0Hz), 1.09 (3H, t, J = 7.0Hz).窨) fe Li 1 8 4- [2- (N-Cyclopropylmethyl-benzenesulfonylamino) -5-tri &lt; fluoromethylphenoxymethyl] cinnamic acid The paper size applies to Chinese national standards ( CNS) A4 specification (210X297 mm) 136 3933 1 523506 A7 B7 V. Description of the invention (137)

C〇〇H TLC ： R f 0.47 (氯仿：甲酵=9:1); NMR ：δ7.80 (1H, d, J=16.0Hz), 7.14-7.55 (10H, m), 7.67 (2H, m), 6.49 (1H, d, J=16.0Hz), 4.88 (2H, s), 3.49 (2H, d, J=7.〇Hz), 0.87 (1 H, m), 0.37 (2H, m), 0.06 (2H, m)〇 審瀹例18 (1 04) 4-[2-(H-異丙基-甲磺醸胺基）-5-三氟甲基苯氧甲基]桂皮 酸C〇H TLC: R f 0.47 (chloroform: formazan = 9: 1); NMR: δ 7.80 (1H, d, J = 16.0Hz), 7.14-7.55 (10H, m), 7.67 (2H, m ), 6.49 (1H, d, J = 16.0Hz), 4.88 (2H, s), 3.49 (2H, d, J = 7.0 Hz), 0.87 (1 H, m), 0.37 (2H, m), 0.06 (2H, m). Examination Example 18 (1 04) 4- [2- (H-isopropyl-methanesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH 〇2S、 TLC : R f 0.47 (氯仿：甲醇=9:1); 經濟部中央標準局員工消費合作社印製 NM R ： δ 7.76 (1 H, d, J=16.0Hz), 7.61 (2H, d, J=8.4Hz), 7.49 (2H, d, J=8.4Hz), 7.37 (3H, m), 6.48 (1H, d, J=16.0Hz), 5.14 (2H, s), 4.31 (1H, m), 2.89 (3H, s), 1.28 (3H, d, J=6.6Hz), 1.09 (3H, d, J=6.6Hz)〇 奮施例is (i os) 苄基-丙磺酿胺基）-5-三氟甲基笨氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 137 3 93 3 1 523506 A7 B7 五、發明説明（138)COOH 〇2S, TLC: R f 0.47 (chloroform: methanol = 9: 1); NM R printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: δ 7.76 (1 H, d, J = 16.0 Hz), 7.61 (2H, d, J = 8.4Hz), 7.49 (2H, d, J = 8.4Hz), 7.37 (3H, m), 6.48 (1H, d, J = 16.0Hz), 5.14 (2H, s), 4.31 (1H, m), 2.89 (3H, s), 1.28 (3H, d, J = 6.6Hz), 1.09 (3H, d, J = 6.6Hz). Example is (i os) benzyl-propanesulfonylamino group ) -5-Trifluoromethylbenzyloxymethyl] cinnamic acid The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 137 3 93 3 1 523506 A7 B7 V. Description of the invention (138)

COOH T L C ： R f 0.29 (氯仿：甲醇：乙酸=100:5:1); NM R ： δ 7.82 (1 H, d, J=16.2Hz), 7.65 (2H, d, J=8.4Hz), 7.51 (2H, d, J=8.4Hz), 7.09-7.31 (8H, m), 6.52 (1H,d, J=16.2Hz), 5.17(2H, s), 4.78 (2H,s), 2.94 (2H, m), [80 (2H，m)，0.85 (2H, t，J=7.4Hz)。 奮 _ 例 1 8 Ofi) 4-[2-(N-丙基-苯磺釀胺基）-4-甲基苯氧甲基]桂皮酸COOH TLC: R f 0.29 (chloroform: methanol: acetic acid = 100: 5: 1); NM R: δ 7.82 (1 H, d, J = 16.2Hz), 7.65 (2H, d, J = 8.4Hz), 7.51 (2H, d, J = 8.4Hz), 7.09-7.31 (8H, m), 6.52 (1H, d, J = 16.2Hz), 5.17 (2H, s), 4.78 (2H, s), 2.94 (2H, m), [80 (2H, m), 0.85 (2H, t, J = 7.4Hz). Fen _ Example 1 Ofi) 4- [2- (N-propyl-benzenesulfonylamino) -4-methylphenoxymethyl] cinnamic acid

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XOOHXOOH

TLC : Ri 0.39 (氯仿··甲醇=9:1); NMR ： 5 7.79 (1H, d, J=16.0Hz), 7.70-7.65 (2H, m), 7.50 (2H, d, J=8.0Hz), 經濟部中央標準局員工消費合作社印製 7.42-7.38 (1H, m), 7.30 (2H, t, J=8.0Hz), 7.16 (2H, d, J=8.0Hz), 7.11 (1H, d, J=1.5Hz), 7.07 (1H, dd, J=1.5, 8.0Hz) , 6.74 (1H, d, J=8.0Hz), 6.47 (1H, d, J=16.0Hz), 4.90-470 (2H, br), 3.70-3.50 (2H, br), 2.29 (3H, s), 1.55-1.45 (2H, m), 0.88 (3H, t, J=7.0Hz)〇 奮施例1 8 ( 1 0 7 ) 4-[2-(N-丙-2-烯基）苯磺醸胺基]-5-三氟甲基苯氧甲基] 桂皮酸 本纸張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 138 3933 1 523506 ΑΊ Β7 五、發明説明（13si)TLC: Ri 0.39 (chloroform · methanol = 9: 1); NMR: 5 7.79 (1H, d, J = 16.0Hz), 7.70-7.65 (2H, m), 7.50 (2H, d, J = 8.0Hz) , Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 7.42-7.38 (1H, m), 7.30 (2H, t, J = 8.0Hz), 7.16 (2H, d, J = 8.0Hz), 7.11 (1H, d, J = 1.5Hz), 7.07 (1H, dd, J = 1.5, 8.0Hz), 6.74 (1H, d, J = 8.0Hz), 6.47 (1H, d, J = 16.0Hz), 4.90-470 (2H, br), 3.70-3.50 (2H, br), 2.29 (3H, s), 1.55-1.45 (2H, m), 0.88 (3H, t, J = 7.0Hz) 〇Example 1 8 (1 0 7) 4- [2- (N-prop-2-enyl) benzenesulfonamido] -5-trifluoromethylphenoxymethyl] cinnamic acid This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 Mm) 138 3933 1 523506 ΑΊ Β7 V. Description of the invention (13si)

(請先閱讀背面之注意事項再填寫本頁) Τ L C ： R f 0.35 (氯仿：甲醇=9:1); NMR ： 5 7.80 (1H, d, J=16.0Hz), 7.71-7.68 (2H, m), 7.54 (2H, d, J=8.0Hz), 7.49-7.45 (1H, m), 7.40 (1H, d, J=8.0Hz), 7.38-7.33 (2H, m), 7.25 (1H, dd, J=2.0, 8.0Hz), 7.19 (2H, d, J=8.0Hz), 7 .12 (1H, d, J=2.0Hz), 6.49 (1H, d, J=16.0Hz), 5.80-5.70 (1H, m), 5.07-5.02 (2H, m), 4.88 (2H, s), 4.5-4.3 (2H, m)〇 奮 _ 例 Ί 8 (1 0 8 ) 4 - [2-[N-(2-甲基丙·2-烯基）苯磺醢胺基]-5-三氟甲基苯 氧甲基]桂皮酸(Please read the notes on the back before filling this page) Τ LC: R f 0.35 (chloroform: methanol = 9: 1); NMR: 5 7.80 (1H, d, J = 16.0Hz), 7.71-7.68 (2H, m), 7.54 (2H, d, J = 8.0Hz), 7.49-7.45 (1H, m), 7.40 (1H, d, J = 8.0Hz), 7.38-7.33 (2H, m), 7.25 (1H, dd , J = 2.0, 8.0Hz), 7.19 (2H, d, J = 8.0Hz), 7.12 (1H, d, J = 2.0Hz), 6.49 (1H, d, J = 16.0Hz), 5.80-5.70 (1H, m), 5.07-5.02 (2H, m), 4.88 (2H, s), 4.5-4.3 (2H, m) 〇 Fen _ Example Ί 8 (1 0 8) 4-[2- (N- ( 2-methylprop · 2-alkenyl) benzenesulfonamido] -5-trifluoromethylphenoxymethyl] cinnamic acid

經濟部中央標準局員工消費合作社印製 TLC ： R f 0.39 (氯仿：甲醇=9:1); NMR ： 5 7.80 (1H, d, J=16.0Hz), 7.68-7.63 (2H, m), 7.54 (2H, d, J=8.0Hz), 7.48-7.44 (1H, m), 7.41 (1H, d, J=8.0Hz), 7.35 (2H, t, J=8.0Hz), 7.25 (1H, dd, J=1.5, 8.0Hz), 7.17 (2H, d, J=8.0Hz ), 7.10 (1H, d, J=1.5Hz), 6.50 (1H, d, J=16.0Hz), 4·84 (2H, s), 4.73 (1 H, s), 4.68 (1H, s), 4.20 (2H, s), 1 _74 (3H, s)。 奮 _ 例 1 8 (1 0 9 ) 4-[2-[N-(丙-2-烯基）-2-咲喃磺醯胺基卜5-甲基苯氧甲基 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ297公釐） 139 3933 1 523506 A7 B7 五、發明説明（1 40) ]苯甲酸TLC printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.39 (chloroform: methanol = 9: 1); NMR: 5 7.80 (1H, d, J = 16.0Hz), 7.68-7.63 (2H, m), 7.54 (2H, d, J = 8.0Hz), 7.48-7.44 (1H, m), 7.41 (1H, d, J = 8.0Hz), 7.35 (2H, t, J = 8.0Hz), 7.25 (1H, dd, J = 1.5, 8.0Hz), 7.17 (2H, d, J = 8.0Hz), 7.10 (1H, d, J = 1.5Hz), 6.50 (1H, d, J = 16.0Hz), 4.84 (2H, s), 4.73 (1 H, s), 4.68 (1H, s), 4.20 (2H, s), 1 _74 (3H, s). Fen_ Example 1 8 (1 0 9) 4- [2- [N- (prop-2-enyl) -2-sulfansulfonylaminomethyl 5-methylphenoxymethyl This paper is in accordance with Chinese national standards (CNS) A4 specification (210 × 297 mm) 139 3933 1 523506 A7 B7 V. Description of the invention (1 40)] benzoic acid

COOHCOOH

NN

02S TLC ： R f 0.21 (己烷：乙酸乙酯=1 : 1 ); NMR ： 5 8.14-8.13 (2H, m), 7.45 (2H, d, J=8.5Hz), 7.28 (1H, m), 7.10 (1H, d, J=7.5Hz), 6.85 (1 H, m), 6.84-6.76 (1 H, m), 6.71 (1 H, s), 6.34 (1 H, m), 5.88-5.79 (1H, m), 5.11-5.02 (4H, m), 4.33 (2H, bs), 2.32 (3H, bs)〇 v m m 4-[2-[H-(2-甲基丙-2-烯基）-2-呋喃磺醢胺基]-5-甲基苯 氧甲基]苯甲酸02S TLC: R f 0.21 (hexane: ethyl acetate = 1: 1); NMR: 5 8.14-8.13 (2H, m), 7.45 (2H, d, J = 8.5Hz), 7.28 (1H, m), 7.10 (1H, d, J = 7.5Hz), 6.85 (1 H, m), 6.84-6.76 (1 H, m), 6.71 (1 H, s), 6.34 (1 H, m), 5.88-5.79 ( 1H, m), 5.11-5.02 (4H, m), 4.33 (2H, bs), 2.32 (3H, bs) 〇vmm 4- [2- [H- (2-methylprop-2-enyl)- 2-furansulfonamido] -5-methylphenoxymethyl] benzoic acid

COOHCOOH

MeMe

(請先閱讀背面之注意事項再填寫本頁) o2s 經濟部中央標準局員工消費合作社印m T L C : R f 0·24 (己烷：乙酸乙酯=1:1); NMR ： δ 8.14-8.13 (2Η, m), 7.44 (2Η, d, J=8Hz), 7.26 (1H, m), 7.13 (1H, d, J=8Hz), 6.82 (1H, m), 6.78-6.69 (1H, m), 6.69 (1H, s), 6.^3 (1H, m), 5.00 (2H, s), 4.76 (1H, dd, J=9.5, 1.5 Hz), 4.30 (2H, bs), 2·32 (3H, s), 1.78 (3H，s)。 奮濂俐1 8 (1 1 1 ) 4-[2-(N-異丁基-苯磺醢胺基）-4-甲基苯氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 140 3933 1 523506 A7 B7 五、發明説明（141)(Please read the precautions on the back before filling this page) o2s Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs m TLC: R f 0 · 24 (hexane: ethyl acetate = 1: 1); NMR: δ 8.14-8.13 (2Η, m), 7.44 (2Η, d, J = 8Hz), 7.26 (1H, m), 7.13 (1H, d, J = 8Hz), 6.82 (1H, m), 6.78-6.69 (1H, m) , 6.69 (1H, s), 6. ^ 3 (1H, m), 5.00 (2H, s), 4.76 (1H, dd, J = 9.5, 1.5 Hz), 4.30 (2H, bs), 2.32 ( 3H, s), 1.78 (3H, s). Fen Li Li 1 8 (1 1 1) 4- [2- (N-isobutyl-benzenesulfonamido) -4-methylphenoxymethyl] cinnamic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specifications (210X297 mm) 140 3933 1 523506 A7 B7 V. Description of the invention (141)

C〇〇H NMR ： 5 7.79 (1H, d, J=1 6.0Hz), 7.70-7.60 (2H, m), 7.50 (2H, d, J=8.0Hz), 7.40-7.35 (1H, m), 7.30-7.20 (2H, m), 7.20-7.10 (3H, m), 7.05 (1H, dd, J=2.0, 8.0Hz), 6.72 (1 H, d, J=8.0Hz), 6.47 (1 H, d, J=1 6.0Hz), 4.9-4.5 (2H, m), 3.5-3.3 (2H, m), 2.29 (3H, s), 1.7-1.6 (1H, m), 1.0-0.8 (6H, m)〇 奮嫵俐1 8 (1 1 2) 4-[2-(H-苄基-甲磺醢胺基）-5-三氟甲基笨氧甲基]桂皮酸COH NMR: 5 7.79 (1H, d, J = 1 6.0Hz), 7.70-7.60 (2H, m), 7.50 (2H, d, J = 8.0Hz), 7.40-7.35 (1H, m), 7.30-7.20 (2H, m), 7.20-7.10 (3H, m), 7.05 (1H, dd, J = 2.0, 8.0Hz), 6.72 (1 H, d, J = 8.0Hz), 6.47 (1 H, d, J = 1 6.0Hz), 4.9-4.5 (2H, m), 3.5-3.3 (2H, m), 2.29 (3H, s), 1.7-1.6 (1H, m), 1.0-0.8 (6H, m ) 〇 Fen Lili 1 8 (1 1 2) 4- [2- (H-benzyl-methanesulfonylamino) -5-trifluoromethylbenzyloxymethyl] cinnamic acid

(請先閲讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH 經濟部中央標準局員工消費合作社印製 NM R ： δ 7.80 (1 H, d, J=16.0Hz), 7.64 (2H, d, J=8.4Hz), 7.48 (2H, d, J=8.4Hz), 7·24 (8H, m)，6.50 (1H，d，J=16.0Hz)，5.18 (2H, s), 4_77 (2H, s), 2·88 (3H, s)。 管倫例1 8 (113) &lt; 4-[2-(N-異丁基-2-呋喃磺醯胺基）-4-甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 141 39 3 3 1 523506 A7 B7 五、發明説明（143COMR printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs: δ 7.80 (1 H, d, J = 16.0Hz), 7.64 (2H, d, J = 8.4Hz), 7.48 (2H, d, J = 8.4Hz ), 7.24 (8H, m), 6.50 (1H, d, J = 16.0Hz), 5.18 (2H, s), 4_77 (2H, s), 2.88 (3H, s). Example of tube 1 8 (113) &lt; 4- [2- (N-Isobutyl-2-furansulfonamido) -4-methylphenoxymethyl] benzoic acid CNS) A4 specification (210X297 mm) 141 39 3 3 1 523506 A7 B7 V. Description of the invention (143

XrXr

C〇〇HC〇〇H

02S02S

TLC ： R f 0.26 (乙酸乙酯··己烷=1:1); NMR ： 5 8.11 (2H, d, J=8Hz), 7.41 (2H, d, J=8Hz), 7.25 7.09 (1H, d, J=2Hz), 7.06 (1H, dt, J=8,2Hz), 6.80 (1H, dd, J=4, 1Hz), 6.76 (1H, d, J=8Hz), 6.31 (1H, dd, J=2, 2Hz), 5.20-4.80 (2H, brs), 3.53 (2H, brs), 2.28 (3H, s), 1.67 (1H, m), 0.92 (6H, brs)〇 管 _ 例 1 8 (1 1 4) 4-[2-(N-異丙基-2-呋喃磺醢胺基）-4-甲基苯氧甲基]苯甲 酸TLC: R f 0.26 (ethyl acetate · hexane = 1: 1); NMR: 5 8.11 (2H, d, J = 8Hz), 7.41 (2H, d, J = 8Hz), 7.25 7.09 (1H, d , J = 2Hz), 7.06 (1H, dt, J = 8,2Hz), 6.80 (1H, dd, J = 4, 1Hz), 6.76 (1H, d, J = 8Hz), 6.31 (1H, dd, J = 2, 2Hz), 5.20-4.80 (2H, brs), 3.53 (2H, brs), 2.28 (3H, s), 1.67 (1H, m), 0.92 (6H, brs). Tube_ Example 1 8 (1 1 4) 4- [2- (N-Isopropyl-2-furansulfonamido) -4-methylphenoxymethyl] benzoic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH TLC:Rf 0.19 (乙酸乙酯：己烷=1:1); 經濟部中央標準局員工消費合作社印裝 NM R ： δ 8.1 2 (2Η, d, J=8Hz), 7.55 (2H, d, J=8Hz), 7.44 (1 H, d, J=2Hz), 7.11 (1 H, dd, J=8, 2Hz), 6.91 (1 H, dd, J=3, 1 Hz), 6.87 (1 H, d, J=3Hz), 6.84 (1 H, d, J=8Hz), 6.42 (1 H, dd, J=3, 1 Hz), 5.10 (2H, s), 4.48 (1 H, m), 2.27 (3H, s), 1.12 (6H, d，J=7Hz)。 &lt; 奮施例1 8 (1 1 5 ) 4-[2-[N-(2-甲基丙-2-烯基）-2-呋喃磺醢胺基]-4-甲基苯 氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 142 39 33 1 523506 A7 B7COOH TLC: Rf 0.19 (ethyl acetate: hexane = 1: 1); NM R printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: δ 8.1 2 (2Η, d, J = 8Hz), 7.55 (2H, d, J = 8Hz), 7.44 (1 H, d, J = 2Hz), 7.11 (1 H, dd, J = 8, 2Hz), 6.91 (1 H, dd, J = 3, 1 Hz), 6.87 (1 H , d, J = 3Hz), 6.84 (1 H, d, J = 8Hz), 6.42 (1 H, dd, J = 3, 1 Hz), 5.10 (2H, s), 4.48 (1 H, m), 2.27 (3H, s), 1.12 (6H, d, J = 7Hz). &lt; Example 1 8 (1 1 5) 4- [2- [N- (2-methylprop-2-enyl) -2-furansulfonamido] -4-methylphenoxymethyl ] Benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) 142 39 33 1 523506 A7 B7

C〇〇HC〇〇H

(請先閲讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

02S TLC ： R f 0.21 (乙酸乙酯··己烷=1 : 1 ); NMR ： 58.12 (2H, d, J=8Hz), 7.42 (2H, d, J=8Hz), 7.26 (1H, m), 7.07 (1H, d, J=2Hz), 7.06 (1 H, dd, J=8, 2Hz), 6.83 (1 H, d, J=3Hz), 6.75 (1 H, d, J=8Hz), 6.33 (1H, dd, J=3, 2Hz), 4.97 (2H, s), 4.77 (2H, s), 4.30 (2H, s), 2.28 (3H, s), 1.79 (3H,s)〇 奮 _ 例 1 8 (1 1 fi) 4-[2-(N-異丙基-2-呋喃磺醯胺基）-5-甲基苯氧甲基]桂皮 酸02S TLC: R f 0.21 (ethyl acetate · hexane = 1: 1); NMR: 58.12 (2H, d, J = 8Hz), 7.42 (2H, d, J = 8Hz), 7.26 (1H, m) , 7.07 (1H, d, J = 2Hz), 7.06 (1 H, dd, J = 8, 2Hz), 6.83 (1 H, d, J = 3Hz), 6.75 (1 H, d, J = 8Hz), 6.33 (1H, dd, J = 3, 2Hz), 4.97 (2H, s), 4.77 (2H, s), 4.30 (2H, s), 2.28 (3H, s), 1.79 (3H, s) Example 1 8 (1 1 fi) 4- [2- (N-isopropyl-2-furansulfonamido) -5-methylphenoxymethyl] cinnamic acid

經濟部中央標準局員工消費合作社印製 TLC ： R f 0.20 (己烷：乙酸乙酯=1 : 1 ); NMR ： 5 7.80 (1H, d, J=16Hz), 7.61-7.45 (4H, m), 7.43 (1H, m), 6.93-6.88 (2H, m), 6.79-6.73 (2H, m), 6.47 (1H, d, J=16Hz), 6.41 (1H/dd, J=3.5, 2Hz), 5.07 (2H, s), 4.56-4.43 (1H, m), 2.34 (3H, s), 1.10 (6H, dd, J=6.5, 4Hz)〇 啻 _ 例 T 8 ( ΐ 1 7 ) 4-[2-(M-異丙基-2-呋喃磺醢胺基）-5-三氟甲基苯氧甲基] 桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 143 39331 A7Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs TLC: R f 0.20 (hexane: ethyl acetate = 1: 1); NMR: 5 7.80 (1H, d, J = 16Hz), 7.61-7.45 (4H, m) , 7.43 (1H, m), 6.93-6.88 (2H, m), 6.79-6.73 (2H, m), 6.47 (1H, d, J = 16Hz), 6.41 (1H / dd, J = 3.5, 2Hz), 5.07 (2H, s), 4.56-4.43 (1H, m), 2.34 (3H, s), 1.10 (6H, dd, J = 6.5, 4Hz) 〇 啻 _ Example T 8 (ΐ 1 7) 4- (2 -(M-Isopropyl-2-furansulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X297 mm) 143 39331 A7

523506 五、發明説明（144) TLC:Rf 0.18 (己烷：乙酸乙酯=1:1); NMR ： 57.80 (1H, d, J=16Hz), 7.63-7.51 (4H, m), 7.46 (1H, dd, J=1.5, 1Hz), 7.23-7.20 (3H, m), 6.94 (1 H, dd, J=3.5, 1 Hz), 6.52-6.43 (3H, m), 5.1 4 (2H, s), 4.51-4.41 (1H, m), 1.09 (6H，dd, J=6.5, 1 Hz)。 奮淪例1 8 (1 T8) 4-[2-(N-異丙基-2-呋喃磺釀胺基）-4-三氟甲基苯氧甲基] 苯甲酸 --------— (請先閱讀背面之注意事項再填寫本頁) 訂523506 V. Description of the invention (144) TLC: Rf 0.18 (hexane: ethyl acetate = 1: 1); NMR: 57.80 (1H, d, J = 16Hz), 7.63-7.51 (4H, m), 7.46 (1H , dd, J = 1.5, 1Hz), 7.23-7.20 (3H, m), 6.94 (1 H, dd, J = 3.5, 1 Hz), 6.52-6.43 (3H, m), 5.1 4 (2H, s) , 4.51-4.41 (1H, m), 1.09 (6H, dd, J = 6.5, 1 Hz). Example 1 (1 T8) 4- [2- (N-Isopropyl-2-furansulfonylamino) -4-trifluoromethylphenoxymethyl] benzoic acid ------- -— (Please read the notes on the back before filling this page)

T L C ： R f 0.35 (乙酸乙酯：己烷：乙酸=50:50:1); 經滴部中央標隼局員工消費合作社印製 NMR ： 58.16 (2H, d, J=8.5Hz), 7.60 (3H, m), 7.38 (1H, dd, J=1.〇. 2.0Hz), 7.26 (1H, m), 7.05 (1H, d, J=9.0Hz), 6.95 (1H, d, J=3.0Hz), 6.47 (1H, dd, J-2.0, 3.5Hz), 5.22 (2H, s), 4·52 (1H,七峯，J=7.0Hz), 1.12 (3H，d, J=7.〇Hz)J.1〇 (3H’ d, J=7.0Hz)〇 奮淪例1 8 ( ΐ 1 9 ) 4-[2-(N-異丁基-2-呋喃磺醸胺基）-4-三氟甲基笨氧甲基] 苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 144 3933 1 523506 A7 B7 五、發明説明（I4今TLC: R f 0.35 (ethyl acetate: hexane: acetic acid = 50: 50: 1); NMR printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Distillation: 58.16 (2H, d, J = 8.5Hz), 7.60 ( 3H, m), 7.38 (1H, dd, J = 1.〇.2.0Hz), 7.26 (1H, m), 7.05 (1H, d, J = 9.0Hz), 6.95 (1H, d, J = 3.0Hz ), 6.47 (1H, dd, J-2.0, 3.5Hz), 5.22 (2H, s), 4.52 (1H, seven peaks, J = 7.0Hz), 1.12 (3H, d, J = 7.〇Hz ) J.1〇 (3H 'd, J = 7.0Hz). Example 1 8 (ΐ 1 9) 4- [2- (N-isobutyl-2-furansulfonamido) -4-triene Fluoromethylbenzyloxymethyl] Benzoic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 144 3933 1 523506 A7 B7 V. Description of the invention (I4 to today

COOHCOOH

T L C ： R f 0.35 (乙酸乙酯··己烷··乙酸=50:50:1); NM R ： δ 8.1 5 (2Η, d, J=9.0Hz), 7.55 (1 H, m), 7.48 (2Η, d, J=9.0Hz), 7.44 (1 H, d, J=2.0Hz), 7.35 (1 H, dd, J=1.0, 2.0Hz), 6.99 (1 H, d, J=9.0Hz), 6.86 (1 H, dd, J=1.0, 2.0Hz), 6.39 (1 H, dd, J=2.0, 4.0Hz), 5.12 (2H, br), 3.52 (2H, d, J=7.0Hz), 1.64 (1H, m)，0.92 (6H，d, J=6.5Hz)。 奮 _ 例 1 8 (120) 4-[2-(N-異丙基-苯磺釀胺基）-4-三氟甲基苯氧甲基]桂皮 酸 (請先閲讀背面之注意事項再填寫本頁)TLC: R f 0.35 (ethyl acetate · hexane ·· acetic acid = 50: 50: 1); NM R: δ 8.1 5 (2Η, d, J = 9.0Hz), 7.55 (1 H, m), 7.48 (2Η, d, J = 9.0Hz), 7.44 (1 H, d, J = 2.0Hz), 7.35 (1 H, dd, J = 1.0, 2.0Hz), 6.99 (1 H, d, J = 9.0Hz ), 6.86 (1 H, dd, J = 1.0, 2.0Hz), 6.39 (1 H, dd, J = 2.0, 4.0Hz), 5.12 (2H, br), 3.52 (2H, d, J = 7.0Hz) , 1.64 (1H, m), 0.92 (6H, d, J = 6.5Hz). Fen_ Example 1 8 (120) 4- [2- (N-Isopropyl-benzenesulfonylamino) -4-trifluoromethylphenoxymethyl] cinnamic acid (Please read the precautions on the back before filling (This page)

經滴部中央標準局員工消費合作社印製 TLC ： R f 0.35 (乙酸乙酯·•己烷：乙酸=5 0 ·· 5 0 ·· 1); NM R ： δ 7.81 (3H, m), 7.58-7.62 (3H, m), 7.53 (1 H, m), 7.49 (2Η, d, J=8.0Hz), 7.41 (2H, m), 7.24 (1H, d,J=2.0Hz), 7.07 (1H, d, J=8.5Hz), 6.49 (1H, d, J=16.5Hz), 5.13 (1H, d, J=1 2.5Hz), 5.12 (1H, d, J=12.5Hz)，4.40 (1H,七峯， J=6.5Hz), 4.07 (3H, d, J=6.5Hz), 1.02 (3H, d, J=6.5Hz)〇 奮 _ 例 1 8 (1 21 ) 4-[2-(H-異丁基-2-呋喃磺醸胺基）-5-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 145 3933 1 523506 A7 B7 五、發明説明（14$Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of TLC: R f 0.35 (ethyl acetate · • hexane: acetic acid = 5 0 ·· 5 0 ·· 1); NM R: δ 7.81 (3H, m), 7.58 -7.62 (3H, m), 7.53 (1 H, m), 7.49 (2Η, d, J = 8.0Hz), 7.41 (2H, m), 7.24 (1H, d, J = 2.0Hz), 7.07 (1H , d, J = 8.5Hz), 6.49 (1H, d, J = 16.5Hz), 5.13 (1H, d, J = 1 2.5Hz), 5.12 (1H, d, J = 12.5Hz), 4.40 (1H, Seven peaks, J = 6.5Hz), 4.07 (3H, d, J = 6.5Hz), 1.02 (3H, d, J = 6.5Hz) 〇 Fen_ Example 1 8 (1 21) 4- [2- (H- Isobutyl-2-furansulfonylamino) -5-chlorophenoxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) 145 3933 1 523506 A7 B7 V. Description of the invention (14 $

CICI

XIXI

XrXr

C〇〇H N〆C〇〇H N〆

02S02S

T L C : R f 0.36 (乙酸乙酯：己烷：乙酸= 50:50:1); NM R ： δ 8.1 4 (2H, d, J=8.5Hz), 7.44 (2H, d, J=8.5Hz), 7.26 (1 H, m), 7.21 (1 H, d, J=9.0Hz), 6.98 (1H, dd, J=2.5, 8.0Hz), 6.91 (1H, d, J=2.5Hz), 6.82 (1H, d, J=4.5Hz), 6.34 (1 H, d, J=2.0, 3.0Hz), 5.00 (2H, br), 3.51 (2H, brs), 1.65 (1 H, m), 0.91 (6H, d, J=6.5Hz)。 奮施例1 1 2 W4-[2-(N-異丙基-2-呋喃磺醣胺基）-5-氯苯氧甲基]桂皮酸TLC: R f 0.36 (ethyl acetate: hexane: acetic acid = 50: 50: 1); NM R: δ 8.1 4 (2H, d, J = 8.5Hz), 7.44 (2H, d, J = 8.5Hz) , 7.26 (1 H, m), 7.21 (1 H, d, J = 9.0Hz), 6.98 (1H, dd, J = 2.5, 8.0Hz), 6.91 (1H, d, J = 2.5Hz), 6.82 ( 1H, d, J = 4.5Hz), 6.34 (1 H, d, J = 2.0, 3.0Hz), 5.00 (2H, br), 3.51 (2H, brs), 1.65 (1 H, m), 0.91 (6H , d, J = 6.5Hz). Example 1 1 2 W4- [2- (N-Isopropyl-2-furansulfosylamino) -5-chlorophenoxymethyl] cinnamic acid

02S02S

(請先閱讀背面之注意事項再填寫本頁) TLC : R f 0.49 (氯仿：甲醇=9:1); 經濟部中央標準局員工消費合作社印製 NM R ： δ 7.80 (1 H, d, J=16.2Hz), 7.60 (2H, d, J=8.4Hz), 7.50 (2H, d, J=8.4Hz), 7.45-7.42 (1 H, m), 7.02-6.90 (4H, m), 6.53-6.40 (2H, m), 5.07 (2H, s), 4.60-4.40 (1H, m), 1.10 (3H, d, J=6.6Hz), 1.07 (3H, d, J=6.6Hz)〇 奮_例18 ( 4-[2-(N-異丁基-2-咲喃碌釀胺基）-5-氯苯氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 146 39 33 1 523506 A7 B7 呋喃磺醢胺基）-5-三氟甲基苯氧甲基] 五、發明説明（147)(Please read the precautions on the back before filling this page) TLC: R f 0.49 (chloroform: methanol = 9: 1); NM R printed by Employee Consumer Cooperative of Central Standard Bureau of Ministry of Economic Affairs: δ 7.80 (1 H, d, J = 16.2Hz), 7.60 (2H, d, J = 8.4Hz), 7.50 (2H, d, J = 8.4Hz), 7.45-7.42 (1 H, m), 7.02-6.90 (4H, m), 6.53- 6.40 (2H, m), 5.07 (2H, s), 4.60-4.40 (1H, m), 1.10 (3H, d, J = 6.6Hz), 1.07 (3H, d, J = 6.6Hz) 18 (4- [2- (N-Isobutyl-2-carbofuranamine) -5-chlorophenoxymethyl] cinnamic acid The paper size is applicable to China National Standard (CNS) A4 (210X297 mm) ) 146 39 33 1 523506 A7 B7 Furansulfonylamino) -5-trifluoromethylphenoxymethyl] 5. Description of the invention (147)

丁 L C : R f 0.49 (氯仿：甲醇=9:1); NM R ： δ 7.80 (1 H, d, J=15.8Hz), 7.58 (2H, d, J=8.0Hz), 7.37 (2H, d, J=8.0Hz), 7.25 (1 H, dd, J=1.0, 1.8Hz), 7.20 (1 H, d, J=8.2Hz), 7.00-6.90 (2H, m), 6.81 (1 H, dd, J=1.0, 3.6Hz), 6.49 (1H, d, J=15.8Hz), 6.33 (1H, dd, J=1.8, 3.6Hz), 4.95 (2H, s), 3.60-3.40 (2H, m), 1.80-1.50 (1H, m), 0.90 (6H, d, J=6.6Hz)〇 奮 _ 例 1 1 ?· 4 ) 4- [2- (N-異丁基 苯甲酸DLC: R f 0.49 (chloroform: methanol = 9: 1); NM R: δ 7.80 (1 H, d, J = 15.8Hz), 7.58 (2H, d, J = 8.0Hz), 7.37 (2H, d , J = 8.0Hz), 7.25 (1 H, dd, J = 1.0, 1.8Hz), 7.20 (1 H, d, J = 8.2Hz), 7.00-6.90 (2H, m), 6.81 (1 H, dd , J = 1.0, 3.6Hz), 6.49 (1H, d, J = 15.8Hz), 6.33 (1H, dd, J = 1.8, 3.6Hz), 4.95 (2H, s), 3.60-3.40 (2H, m) , 1.80-1.50 (1H, m), 0.90 (6H, d, J = 6.6Hz) 〇 Fen _ Example 1 1 ~ 4) 4- [2- (N-isobutylbenzoic acid

C〇〇H (請先閲讀背面之注意事項再填寫本頁) F3C\^\^aC〇〇H (Please read the notes on the back before filling this page) F3C \ ^ \ ^ a

經濟部中央標準局員工消費合作社印製 TLC ： R f 0.20 (己烷··乙酸乙酯=1 : 1 ); NMR ：δ8.18-8.14 (2H, m), 7.48-7.40 (2H, m), 7.30-7.26 (2H, m), 7.16 (1H, m), 6.84 (1 H, dd, J=3.5,1 Hz), 6.35 (1 H, dd, J=3.5, 2Hz), 5.07 (2H, s), 3.54 (2H, d, J=7Hz), 1 ·64 (1 H,七峯，J=7Hz)，0.90 (6H, d，J=7Hz)。 謇施例1 8 ( 1 2 R ) 4-[2-(N-異丁基-2-呋喃磺醸胺基）-4-氯苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 147 39 3 3 1 523506 A7 B7 五、發明説明（148)TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.20 (hexane ·· ethyl acetate = 1: 1); NMR: δ 8.18-8.14 (2H, m), 7.48-7.40 (2H, m) , 7.30-7.26 (2H, m), 7.16 (1H, m), 6.84 (1 H, dd, J = 3.5, 1 Hz), 6.35 (1 H, dd, J = 3.5, 2Hz), 5.07 (2H, s), 3.54 (2H, d, J = 7Hz), 1.64 (1 H, seven peaks, J = 7Hz), 0.90 (6H, d, J = 7Hz).謇 例 1 8 (1 2 R) 4- [2- (N-isobutyl-2-furansulfonamido) -4-chlorophenoxymethyl] benzoic acid The paper size is applicable to Chinese national standards (CNS ) A4 specification (210X297 mm) 147 39 3 3 1 523506 A7 B7 V. Description of the invention (148)

C〇〇HC〇〇H

ClCl

02S TLC ： R f 0.36 (氛仿·•甲醇= 9:1); NMR : δ 8.14 (2H，d, J=8.4Hz)，7.44 (2H，d，J=8.4Hz)，7.34-7.20 (3H，m), 6.90-6.80 (2H, m), 6.37 (1H, dd, J=1.8, 3.0Hz), 5.03 (2H, s), 3.51 (2H, d, J=7.2Hz), 1.80-1.50 (1H, m), 0.91 (6H, d, J=6.6Hz)〇 奮撫例i 4-[2_(H-異丁基-2-呋喃磺釀胺基）-4 -甲基苯氧甲基]桂皮 酸 (請先閱讀背面之注意事項再填寫本頁) o2s02S TLC: R f 0.36 (Fluent · Methanol = 9: 1); NMR: δ 8.14 (2H, d, J = 8.4Hz), 7.44 (2H, d, J = 8.4Hz), 7.34-7.20 (3H , M), 6.90-6.80 (2H, m), 6.37 (1H, dd, J = 1.8, 3.0Hz), 5.03 (2H, s), 3.51 (2H, d, J = 7.2Hz), 1.80-1.50 ( 1H, m), 0.91 (6H, d, J = 6.6Hz). Example 1 4- [2_ (H-isobutyl-2-furansulfonylamino) -4-methylphenoxymethyl] Cinnamic acid (please read the notes on the back before filling this page) o2s

經濟部中央標準局員工消費合作社印製 TLC : R f 0.33 '(氯仿：甲醇=9:1); NM R ： δ 7.80 (1H, d, J=16.0Hz), 7.57 (2H, d, J=8.0Hz), 7.36 (2H, d, J=8.0Hz), 7.28-7.22 (1H, m), 7.12-7.02 (2H, m), 6.84-6.74 (2H, m), 6.48 (1H, d, J=16.0Hz), 6.32 (1H, dd, J=1.8, 3.6Hz), 4.92 (2H, s), 3.54 (2H, d, J=7.0Hz), 2.28 (3H, s), 1.80-1.60 (1H, m), 0.92 (6H, d, J=6.6Hz)〇 奮 _ 例 1 8 M 2 7 ) 4-[2-(N-異丁基-4-乙氧基苯磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 148 39 3 3 1 523506 A7 B7 五、發明説明（1 49)Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.33 '(chloroform: methanol = 9: 1); NM R: δ 7.80 (1H, d, J = 16.0Hz), 7.57 (2H, d, J = 8.0Hz), 7.36 (2H, d, J = 8.0Hz), 7.28-7.22 (1H, m), 7.12-7.02 (2H, m), 6.84-6.74 (2H, m), 6.48 (1H, d, J = 16.0Hz), 6.32 (1H, dd, J = 1.8, 3.6Hz), 4.92 (2H, s), 3.54 (2H, d, J = 7.0Hz), 2.28 (3H, s), 1.80-1.60 (1H , m), 0.92 (6H, d, J = 6.6Hz). Example 1 8 M 2 7) 4- [2- (N-isobutyl-4-ethoxybenzenesulfonamido) -5 -Trifluoromethylphenoxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 148 39 3 3 1 523506 A7 B7 V. Description of the invention (1 49)

COOH ί^ΥΟ2▲丫^ ^^〇c2h5 TLC ： R f 0.35 (氯仿：甲醇··乙酸=1 〇 〇 ·· 5 : 1 ); NM R ： δ 8.09 (2Η, d, J=8.5Hz), 7.52 (2H, d, J=8.5Hz), 7.46 (1 H, d, J=8.5Hz), 7.25-7.29 (3H, m), 7.13 (1 H, brd, J=1.5Hz), 6.73 (2H, d, J=9.0Hz), 4.92 (2H, br), 3.96 (2H, q, J=7.5Hz), 3.40 (2H, brs), 1.59 (1 H, m), 1.42 (3H, t, J=7.5Hz), 0.90 (6H，brd，J=6.0Hz)。 g _ 俐 1 8 M 28)4-[2-(N-甲基-苯磺釀胺基）-4-氯苯氧甲基]苯甲酸COOH ί ^ ΥΟ2 ▲ 丫 ^ ^^ 〇c2h5 TLC: R f 0.35 (chloroform: methanol · · acetic acid = 1 〇 ·· 5: 1); NM R: δ 8.09 (2Η, d, J = 8.5Hz), 7.52 (2H, d, J = 8.5Hz), 7.46 (1 H, d, J = 8.5Hz), 7.25-7.29 (3H, m), 7.13 (1 H, brd, J = 1.5Hz), 6.73 (2H , d, J = 9.0Hz), 4.92 (2H, br), 3.96 (2H, q, J = 7.5Hz), 3.40 (2H, brs), 1.59 (1 H, m), 1.42 (3H, t, J = 7.5Hz), 0.90 (6H, brd, J = 6.0Hz). g _ Li 1 8 M 28) 4- [2- (N-methyl-benzenesulfonylamino) -4-chlorophenoxymethyl] benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

CICI

02S 經瀦部中央標準局員工消費合作社印t T L C ： R f 0.43 (氯仿：甲酵：水=9 ·· 1 : 〇 . 1 ); NMR (DMSO-d6) ：δ 7.88 (2H, d, J=8.6Hz), 7.66-7.38 (6H, m), 7.25-7.11 (4H, m), 4.95 (2H, s), 3.15 (3H, s)〇 y _ 例 194-[2-(N-環戊基甲基-苯磺醯胺基）-5-三氟甲基笨氧甲基] 苯甲酸甲酯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 149 3933 1 523506 A7 B7 五、發明説明（1 50)02S Consumer Cooperative Cooperatives, Central Bureau of Standards, Ministry of Economic Affairs, TLC: R f 0.43 (chloroform: formazan: water = 9 · · 1: 〇. 1); NMR (DMSO-d6): δ 7.88 (2H, d, J = 8.6Hz), 7.66-7.38 (6H, m), 7.25-7.11 (4H, m), 4.95 (2H, s), 3.15 (3H, s) 〇y _ Example 194- [2- (N-cyclopentane Methylmethyl-benzenesulfonylamino) -5-trifluoromethylbenzyloxymethyl] methyl benzoate This paper is sized for China National Standard (CNS) A4 (210X 297 mm) 149 3933 1 523506 A7 B7 V. Description of the invention (1 50)

F3CF3C

COOMe (請先閱讀背面之注意事項再填寫本頁) 4-(2-苯磺醢胺基-5-三氟甲基苯氧甲基）苯甲酸甲酯 (251iag;由實施例15合成）、三苯膦（142fflg)及環戊基甲醇 (54mg)之THF(2ial)溶液中，在0¾下添加偶氮二羧酸二乙 酿（89μΠ下文簡稱DEAD),於室溫攪拌隔夜。反應液K 矽膠管柱層析法（己烷：乙酸乙酯=7:1)純化，得具下列物 理數據之標題化合物（3 3 3 mg)。 TLC: Rf 0.51(己烷：乙酸乙酯= 3:1); NMR:S8.01(2H,d，J=8.4Hz),7.63-7.58(2H,m)，7.48-7.25(5H,m), 7.17(2H,d,J=8.4Hz), 7.09(lH,d,J=1.4Hz) ,4.83(2H,br),3.95(3H,s),3.55(2H,d-like),1.92-1.09(9H,n) 奮_例20 經滴部中央標準局員工消費合作社印製 4-[2-(N-環戊基甲基-苯磺醸胺基）-5-三氟甲基苯氧甲基] 苯甲酸COOMe (Please read the precautions on the back before filling out this page) 4- (2-benzenesulfonamido-5-trifluoromethylphenoxymethyl) benzoic acid methyl ester (251iag; synthesized from Example 15), To a solution of triphenylphosphine (142fflg) and cyclopentylmethanol (54mg) in THF (2ial), diethyl azodicarboxylate (89μΠ hereinafter referred to as DEAD) was added at 0¾, and the mixture was stirred overnight at room temperature. The reaction solution K was purified by silica gel column chromatography (hexane: ethyl acetate = 7: 1) to obtain the title compound (3.33 mg) having the following physical data. TLC: Rf 0.51 (hexane: ethyl acetate = 3: 1); NMR: S8.01 (2H, d, J = 8.4Hz), 7.63-7.58 (2H, m), 7.48-7.25 (5H, m) , 7.17 (2H, d, J = 8.4Hz), 7.09 (lH, d, J = 1.4Hz), 4.83 (2H, br), 3.95 (3H, s), 3.55 (2H, d-like), 1.92- 1.09 (9H, n) Fen_ Example 20 4- [2- (N-Cyclopentylmethyl-benzenesulfonamido) -5-trifluoromethylphenoxy was printed by the Consumer Cooperative of the Central Standards Bureau of Didi Methyl] benzoic acid

COOH 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 150 393 3 1 經濟部中央標準局員工消費合作社印製 523506 A7 B7 ____ '____________ 圓&quot;&quot; 五、發明説明（1H) 使用4-[2-(N-環戊基甲基-笨磺酿胺基）_5-二氟甲基 笨氧甲基]笨甲酸甲酯（由實施例19合成），依實施例2之相 同操作，得具下列物理數據之標題化合物。 TLC: Rf 〇.40(氯仿：甲醇：水=9:1:〇·1); NMR:S8.09(2H,d，J=8.2Hz),7.65-7.61(2H，m)，7.47-7*20(7H，ni),7.11(lH,d,J = 1.8Hz)，4.89(2H，br)，3.59- 3·5ΐ(2Η,ιπ)，1·93*&quot;1·1〇(9Η，πΟ gjfe 例；-20 (30) 使用對應化合物，依參考例6 —參考例74實施例74 實施例194實施例2或依參考例參考例9 —參考例I0 — 實施例實施例194實施例2之相同操作，獲得具下列物 理數據之標題化合物。 董_施锎2 0 Π ) 4-[2-(H-環丙基甲基-笨磺醸胺基卜卜三鎮甲基苯氧甲基]COOH This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 150 393 3 1 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 523506 A7 B7 ____ '____________ Circle &quot; &quot; ) 4- [2- (N-cyclopentylmethyl-benzylsulfonylamino) _5-difluoromethylbenzyloxymethyl] benzylcarboxylate (synthesized from Example 19) By the same operation, the title compound having the following physical data was obtained. TLC: Rf 0.40 (chloroform: methanol: water = 9: 1: 〇 · 1); NMR: S8.09 (2H, d, J = 8.2Hz), 7.65-7.61 (2H, m), 7.47-7 * 20 (7H, ni), 7.11 (lH, d, J = 1.8Hz), 4.89 (2H, br), 3.59-3 · 5ΐ (2Η, ιπ), 1.93 * &quot; 1 · 1〇 (9Η ΠΟ gjfe Example; -20 (30) Use the corresponding compound according to Reference Example 6-Reference Example 74 Example 74 Example 194 Example 2 or according to Reference Example Reference Example 9-Reference Example I0-Example Example 194 Example The same operation as 2 was performed to obtain the title compound with the following physical data. Dong_Shi 锎 2 0 Π) 4- [2- (H-Cyclopropylmethyl-benzylsulfonylaminobenzophenone trimethylphenoxymethyl base]

T L C ： R f 0.43 (氯仿：甲醇：水=9 ·· 1 : 0 · 1)〆 NMR ：δ 8.09 (2Η, d, J=8.2Hz), 7.70-7.65 (2H, m), 7.54-7.22 (7H, m), 7.14 (1H, d, J=1.8Hz), 4.93 (2H, s), 3.51 (2H, d, J=7.2Hz), 0.96-0.81 (1H, m), 0.44-0.35 (2H, m), 0.10-0.02 (2H, m)〇 g 淪例 2 0 ( 2 ) _ (請先閱讀背面之注意事項再填寫本頁) 裝· 訂 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 151 3933 1 經濟部中央標準局員工消費合作社印製 523506 A7 ______B7__ 五、發明説明52) 4-[2-(H-第三丁基甲基-苯磺醢胺基）-5-三氟甲基苯氧甲 基]苯甲酸TLC: R f 0.43 (chloroform: methanol: water = 9 ·· 1: 0 · 1) 〆NMR: δ 8.09 (2Η, d, J = 8.2Hz), 7.70-7.65 (2H, m), 7.54-7.22 ( 7H, m), 7.14 (1H, d, J = 1.8Hz), 4.93 (2H, s), 3.51 (2H, d, J = 7.2Hz), 0.96-0.81 (1H, m), 0.44-0.35 (2H , m), 0.10-0.02 (2H, m) 〇g Example 2 0 (2) _ (Please read the precautions on the back before filling out this page) The size of the paper used for binding and binding is applicable to China National Standard (CNS) A4 (210X297 mm) 151 3933 1 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 523506 A7 ______B7__ V. Description of the invention 52) 4- [2- (H-Third-butylmethyl-benzenesulfonamido) -5-three Fluoromethylphenoxymethyl] benzoic acid

TLC : R f 0.5 (氯仿：甲醇=9 : 1); NM R ：δ8.12 (2H, d, J=8.0Hz), 7.6-7.4 (4H, m), 7.4-7.2 (5H, m), 7.09 (1 H, d, J=1.8Hz), 5.02 (1H, d, J=12.4Hz), 4.72 (1H, d, J=12.4Hz), 3.53 (2H, s), 0.86 (9H，s)。TLC: R f 0.5 (chloroform: methanol = 9: 1); NM R: δ8.12 (2H, d, J = 8.0Hz), 7.6-7.4 (4H, m), 7.4-7.2 (5H, m), 7.09 (1 H, d, J = 1.8Hz), 5.02 (1H, d, J = 12.4Hz), 4.72 (1H, d, J = 12.4Hz), 3.53 (2H, s), 0.86 (9H, s) .

T L C : R f 0.47 (氯仿：甲酵··乙酸=100:5:1); NMR:5 7.79 (2H，d，J=7.6Hz)，7.20-7.50 (10H，m)，5.01 (2H，s)，4·28 (1H,七峯， J=6.6Hz), 3.71 (2H, s), 1.08 (3H, d, J=6.6Hz), 1.01 (3H, d, J=6.6Hz)〇 鬣一施…例20 (4) 4-[2-(N-異丙基-丙磺醢胺基）-5-三氟甲基苯氧甲基]苯甲 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐) ' ~ 152 39331 --------眷衣-- (請先閲讀背面之注意事項再填寫本頁)TLC: R f 0.47 (chloroform: formazan · acetic acid = 100: 5: 1); NMR: 5 7.79 (2H, d, J = 7.6Hz), 7.20-7.50 (10H, m), 5.01 (2H, s ), 4 · 28 (1H, 7 peaks, J = 6.6Hz), 3.71 (2H, s), 1.08 (3H, d, J = 6.6Hz), 1.01 (3H, d, J = 6.6Hz) Example 20 (4) 4- [2- (N-isopropyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzyl This paper is sized to the Chinese National Standard (CNS) A4 Specifications (210X297 mm) '~ 152 39331 -------- Family Clothing-(Please read the precautions on the back before filling this page)

、1T 523506 A7 B7 五、發明説明（15含 酸1T 523506 A7 B7 V. Description of the invention (15 contains acid

COOH T L C : R f 0.33 (氯仿：甲酵=2 0 : 1 ); NMR (CD^CI) ： δ 8.13 (2Η, d, J=8.0Hz), 7.54 (2H, d, J=8.0Hz), 7.30-7.46 (3H, m), 5.19 (2H, s), 4.32 (1 H, t*, J=6.2Hz), 2.96 (2H, m), 1.78 (2H, m), 1.27 (2H, d, J=6.4Hz), 1.12 (2H, d, J=6.4Hz), 0.85 (3H, t, J=7.4Hz)〇 g _ 俐 2 o ( 4-[2-(N-異丙基-戊磺酿胺基）-5-三氟甲基苯氧甲基]苯甲 酸COOH TLC: R f 0.33 (chloroform: formazan = 2 0: 1); NMR (CD ^ CI): δ 8.13 (2Η, d, J = 8.0Hz), 7.54 (2H, d, J = 8.0Hz), 7.30-7.46 (3H, m), 5.19 (2H, s), 4.32 (1 H, t *, J = 6.2Hz), 2.96 (2H, m), 1.78 (2H, m), 1.27 (2H, d, J = 6.4Hz), 1.12 (2H, d, J = 6.4Hz), 0.85 (3H, t, J = 7.4Hz) 〇g _ Li 2 o (4- [2- (N-isopropyl-pentanesulfonate Amino group) -5-trifluoromethylphenoxymethyl] benzoic acid

COOH 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) TLC : R f 0·4〇（氯仿·•甲醇=20 :㈠； NMR (CD^CI) ： δ 8.17 (2Η, d, J=8.4Hz), 7.59 (2H, d, J=8.4Hz), 7.12-7.41 (3H, m), 5.18 (2H，s), 4·32 (1H,七峯，J=6.6Hz), 2.97 (2H, m), 1.74 (2H, m), 1.02-1.35 (8H, m), 0·82 (3H, t, J=6.8Hz)。 奮_例2〇 (in 4 - [2-(N-異丙基-丁磺醢胺基）-5-三氟甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 153 3933 1 523506 A7 B7 五、發明説明（154Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) TLC: R f 0 · 4〇 (chloroform · • methanol = 20: ㈠; NMR (CD ^ CI): δ 8.17 (2Η, d, J = 8.4Hz), 7.59 (2H, d, J = 8.4Hz), 7.12-7.41 (3H, m), 5.18 (2H, s), 4.32 (1H, seven peaks, J = 6.6Hz), 2.97 (2H, m), 1.74 (2H, m), 1.02-1.35 (8H, m), 0 · 82 (3H, t, J = 6.8Hz). Fen_Example 2〇 (in 4 -[2- (N-Isopropyl-butanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid The paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 153 3933 1 523506 A7 B7 V. Description of the invention (154

COOH TLC ： R f 0.40 (氯仿：甲酵=9 : 1); .. NM R ： δ 8.1 7 (2Η, d, J=8.2Hz), 7.59 (2H, d, J=8.2Hz), 7.40 (1 H, d, J=7.8Hz), 7.3- 7.2 (2H, m), 5.18 (2H, s), 4.4-4.2 (1 H, m), 3.1 -2.9 (2H, m), 1.8-1.6 (2H, m), 1.4- 1.0 (8H, m), 0.92 (3H，t, J=7.2Hz)。 奮施例20 (7) 4-[2-(N-異丙基-己磺醸胺基）-5-三氟甲基苯氧甲基]苯甲 酸COOH TLC: R f 0.40 (chloroform: formazan = 9: 1); .. NM R: δ 8.1 7 (2Η, d, J = 8.2Hz), 7.59 (2H, d, J = 8.2Hz), 7.40 ( 1 H, d, J = 7.8Hz), 7.3- 7.2 (2H, m), 5.18 (2H, s), 4.4-4.2 (1 H, m), 3.1 -2.9 (2H, m), 1.8-1.6 ( 2H, m), 1.4- 1.0 (8H, m), 0.92 (3H, t, J = 7.2Hz). Example 20 (7) 4- [2- (N-Isopropyl-hexanesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid

COOH T L C : R f 〇.44 (氯仿：甲醇= 9:1); , NM R ： δ 8.1 8 (2Η, d, J=8.0Hz), 7.59 (2H, d, J=8.0Hz), 7.40 (1 H, d, J=8.0Hz), 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 7.3- 7.2 (2H, m), 5.18 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 1.8-1.6 (2H, m), 1.3- 1.0 (12H, m), 0.85 (3H, t, J=7.4Hz)〇 啻施例20 (8) 、 4-[2-(N-異丙基-庚磺醢胺基）-5-三氟甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 154 3 9 3 3 1 523506 A7 B7COOH TLC: R f 〇.44 (chloroform: methanol = 9: 1);, NM R: δ 8.1 8 (2 ,, d, J = 8.0Hz), 7.59 (2H, d, J = 8.0Hz), 7.40 ( 1 H, d, J = 8.0Hz), printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 7.3- 7.2 (2H, m), 5.18 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 1.8-1.6 (2H, m), 1.3- 1.0 (12H, m), 0.85 (3H, t, J = 7.4Hz) 〇 啻Example 20 (8), 4- [2- (N-Isopropyl-heptylsulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 Specifications (210X297 mm) 154 3 9 3 3 1 523506 A7 B7

羥基苯磺醯胺基）-5-三氟甲基苯氧甲 五、發明説明（1 5Hydroxybenzenesulfonylamino) -5-trifluoromethylphenoxymethyl 5. Description of the invention (1 5

COOH TLC : R f 0.48 (氯仿：甲醇=9:1); NM R ： δ 8.1 8 (2Η, d, J=8.0Hz), 7.59 (2H, d, J=8.0Hz), 7.40 (1 H, d, J=8.0Hz), 7.3- 7.2 (2H, m), 5.18 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 1.9-1.6 (2H, m), 1.4- 1.0 (14H, m), 0.86 (3H, t, J=6.2Hz)〇 實施例20 (9) 4- [2- (N-異丙基 基]苯甲酸COOH TLC: R f 0.48 (chloroform: methanol = 9: 1); NM R: δ 8.1 8 (2Η, d, J = 8.0Hz), 7.59 (2H, d, J = 8.0Hz), 7.40 (1 H, d, J = 8.0Hz), 7.3- 7.2 (2H, m), 5.18 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 1.9-1.6 (2H, m ), 1.4- 1.0 (14H, m), 0.86 (3H, t, J = 6.2Hz). Example 20 (9) 4- [2- (N-isopropyl) benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁) 〇 NIS 30 7COOH (Please read the notes on the back before filling this page) 〇 NIS 30 7

U0H 經濟部中央標準局員工消費合作社印製 TLC ： R f 0.28 (氯仿：甲醇=9 : 1)，· NM R ：δ8.13 (2H, d, J=8.2Hz), 7.66 (2H, d, J=9.2Hz), 7.50 (2H, d, J=8.2Hz), 7.3-7.2 (3H, m), 6.72 (2H, d, J=9.2Hz), 5.10 (2H, s), 4.4-4.2 (1 H, m), 3.0-1.5 (2H, br), 1.10 (3H, d, J=6.6Hz), 1·03 (3H, d, J=6.6Hz)。 實 A-M20(10) 4-[2-(N-異丙基-丁磺醢胺基）-5-甲基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 155 3 933 1 523506 A7 B7 五、發明説明（1 56)U0H TLC printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.28 (chloroform: methanol = 9: 1), · NM R: δ8.13 (2H, d, J = 8.2Hz), 7.66 (2H, d, J = 9.2Hz), 7.50 (2H, d, J = 8.2Hz), 7.3-7.2 (3H, m), 6.72 (2H, d, J = 9.2Hz), 5.10 (2H, s), 4.4-4.2 ( 1 H, m), 3.0-1.5 (2H, br), 1.10 (3H, d, J = 6.6Hz), 1.03 (3H, d, J = 6.6Hz). Real A-M20 (10) 4- [2- (N-isopropyl-butanesulfonylamino) -5-methylphenoxymethyl] benzoic acid The paper size is applicable to China National Standard (CNS) A4 specifications ( 210X 297 mm) 155 3 933 1 523506 A7 B7 V. Description of the invention (1 56)

〇2S\^\^〇2S \ ^ \ ^

COOH TXC : R f 0.41 (氛仿：甲酵=9 ·· 1); NMR ： 58.15 (2H, d, J=8.6Hz), 7.57 (2H, d, J=8.6Hz), 7.15 (1H, d, J=8.4Hz), 6.9-6.8 (2H, m), 5.13 (2H,s), 4.4-4.2 (1H, m), 3.1-2.9 (2H, m), 2.36 (3H,s), 1.8-1·6 (2H, m), 1.3-1.2 (5H, m)，1.10 (3H, d, J=6.6Hz), 0.81 (3H, t, J=7.4Hz)。 奮嫵例20 (Ϊ1) 4-[2-(N-異丙基-己磺釀胺基）-5 -甲基苯氧甲基]苯甲酸COOH TXC: R f 0.41 (Aromatic imitation: formazan = 9 · · 1); NMR: 58.15 (2H, d, J = 8.6Hz), 7.57 (2H, d, J = 8.6Hz), 7.15 (1H, d , J = 8.4Hz), 6.9-6.8 (2H, m), 5.13 (2H, s), 4.4-4.2 (1H, m), 3.1-2.9 (2H, m), 2.36 (3H, s), 1.8- 1.6 (2H, m), 1.3-1.2 (5H, m), 1.10 (3H, d, J = 6.6Hz), 0.81 (3H, t, J = 7.4Hz). Example 20 (妩 1) 4- [2- (N-Isopropyl-hexanesulfonylamino) -5 -methylphenoxymethyl] benzoic acid

COOH T L C ： R f 0.47 (氯仿：甲醇=9:1); NM R ： δ 8.15 (2Η, d, J=8.4Hz), 7.57 (2H, d, J=8.4Hz), 7.15 (1 H, d, J=8.4Hz), 7.1 -7.0 (2H, m), 5.13 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 2.36 (3H, s), 1.8-1.6 (2H, m), 1.3-1.0 (12H, m), 0.84 (3H, t, J=6.4Hz)〇 經滴部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 音_例20 (12丄 4-[2-(N-異丙基-庚磺醸胺基）-5 -甲基苯&lt;氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 156 3933 1 523506 A7 B7COOH TLC: R f 0.47 (chloroform: methanol = 9: 1); NM R: δ 8.15 (2Η, d, J = 8.4Hz), 7.57 (2H, d, J = 8.4Hz), 7.15 (1 H, d , J = 8.4Hz), 7.1 -7.0 (2H, m), 5.13 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 2.36 (3H, s), 1.8 -1.6 (2H, m), 1.3-1.0 (12H, m), 0.84 (3H, t, J = 6.4Hz) 〇 Printed by the Consumers' Cooperative of Didi Central Bureau of Standards (Please read the notes on the back before filling (This page) 音 _ 例 20 (12 丄 4- [2- (N-isopropyl-heptylsulfonamido) -5 -methylbenzene &lt; oxymethyl] benzoic acid This paper is applicable to Chinese national standards ( CNS) A4 size (210X 297 mm) 156 3933 1 523506 A7 B7

五、發明説明（1 5V. Description of the invention (1 5

COOH 丁 LC : R f 〇·47 (氛仿：甲醇=9:1); NM R ： δ 8.15 (2Η, d, J=8.0Hz), 7.57 (2H, d, J=8.0Hz), 7.15 (1 H, d, J=8.4Hz), 6.9-6.8 (2H, m), 5.13 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 2.36 (3H, s), 1.9-1.6 (2H, m), 1.3-1.0 (14H, m), 0.85 (3H, t, J=6.2Hz)〇 奮 _ 例 2 0 (1 3 ) 4-[2-(N-異丙基-甲磺醢胺基）-5-甲基苯氧甲基]苯甲酸COOH butyl LC: R f 〇.47 (methanol: 9: 1); NM R: δ 8.15 (2Η, d, J = 8.0Hz), 7.57 (2H, d, J = 8.0Hz), 7.15 ( 1 H, d, J = 8.4Hz), 6.9-6.8 (2H, m), 5.13 (2H, s), 4.4-4.2 (1 H, m), 3.0-2.9 (2H, m), 2.36 (3H, s), 1.9-1.6 (2H, m), 1.3-1.0 (14H, m), 0.85 (3H, t, J = 6.2Hz) 〇 Fen_ Example 2 0 (1 3) 4- [2- (N- Isopropyl-methanesulfonylamino) -5-methylphenoxymethyl] benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁) Θ Μ 〇 NIS 2 〇 7 經滴部中央標準局員工消費合作社印製 TLC : R f 0.13 (己烷：乙酸乙酯=1 ·· 1); NMR : δ 8.17-8.13 (2H，m)，7.58-7.53 (2H，m), 7.17-7.12(1 H，m)，6.8 (2H, m)， 5·1 (2H，m)，4.33 (1H，t峯，J=6.5Hz)，2.90 (3H，s)，2·36 (3H，s)，1.26 (3H，d, J=6.5Hz), 1.09 (3H, d, J=6.5Hz)〇 奮施例20 (14) 4-[2-(N-異丙基-乙磺醢胺基）-5-甲基苯嗜甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） 157 3933 1 523506 A7 B7 五、發明説明（158)COOH (Please read the notes on the back before filling this page) Θ Μ 〇NIS 2 〇7 TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of Didi: R f 0.13 (hexane: ethyl acetate = 1 ·· 1) ; NMR: δ 8.17-8.13 (2H, m), 7.58-7.53 (2H, m), 7.17-7.12 (1 H, m), 6.8 (2H, m), 5.1 (2H, m), 4.33 ( 1H, t peak, J = 6.5Hz), 2.90 (3H, s), 2.36 (3H, s), 1.26 (3H, d, J = 6.5Hz), 1.09 (3H, d, J = 6.5Hz) 〇Fen Example 20 (14) 4- [2- (N-Isopropyl-Ethylsulfonamido) -5-methylbenzene methylophilic] benzoic acid The paper size is applicable to China National Standard (CNS) A4 specifications (210 × 297 mm) 157 3933 1 523506 A7 B7 V. Description of the invention (158)

COOH T L C ： R f 0.20 (己烷：乙酸乙酯=1 ·· 1); NMR ： 5 8.17-8.13 (2H, m), 7.59-7.55 (2H, m), 7.17-7.13 (1 H, m), 6.8 (2H, m), 5·1 (2H, m), 4.33 (1 H,七峯，」=71-^)，3.01(2吨9，」=7心)，2.36(3叶3)，1.29-1.20 (6H, m), 1.09 (3H, d, J=6.5Hz)〇 奮淪例2 0 (1 5 ) 4-[2-(N-異丙基-2-苯乙基磺醢胺基）-5 -甲基苯氧甲基]苯 甲酸COOH TLC: R f 0.20 (hexane: ethyl acetate = 1 ·· 1); NMR: 5 8.17-8.13 (2H, m), 7.59-7.55 (2H, m), 7.17-7.13 (1 H, m) , 6.8 (2H, m), 5.1 · 2 (2H, m), 4.33 (1 H, seven peaks, "= 71- ^), 3.01 (2 tons 9," = 7 hearts), 2.36 (3 leaves 3) ， 1.29-1.20 (6H, m), 1.09 (3H, d, J = 6.5Hz). Example 2 0 (1 5) 4- [2- (N-isopropyl-2-phenethylsulfonium Amine) -5 -methylphenoxymethyl] benzoic acid

〇2S〇2S

COOH TLC ： R f 0.24 (己烷•·乙酸乙酯=1 ·· 1); 經滴部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) NMR ： δ 8.00-7.96 (2Η, m), 7.44-7.40 (2H, m), 7.26-7.14 (4H} m), 7.05-7.01 (2H, m), 6.85-6.81 (2H, m), 5.07 (2H, s), 4.42-4.27 (1 H, m), 3.4-3.2 (2H, m), 3.2-3.0 (2H, m), 2.36 (3H, s), 1.25 (3H, d, J=6.5Hz ), 1.09 (3H, d, J=6.5Hz)〇 奮 _ 例 20(1 fi) 4-[2-(N -異丙基-苯甲基磺醢胺基）-5 -甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 158 39 33 1 523506 A7 B7COOH TLC: R f 0.24 (hexane • · ethyl acetate = 1 ·· 1); Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Distillation (Please read the precautions on the back before filling this page) NMR: δ 8.00- 7.96 (2Η, m), 7.44-7.40 (2H, m), 7.26-7.14 (4H) m), 7.05-7.01 (2H, m), 6.85-6.81 (2H, m), 5.07 (2H, s), 4.42-4.27 (1 H, m), 3.4-3.2 (2H, m), 3.2-3.0 (2H, m), 2.36 (3H, s), 1.25 (3H, d, J = 6.5Hz), 1.09 (3H , d, J = 6.5Hz) Example 20 (1 fi) 4- [2- (N -isopropyl-benzylsulfonamido) -5 -methylphenoxymethyl] benzoate Paper size applies to China National Standard (CNS) A4 (210X297 mm) 158 39 33 1 523506 A7 B7

五、發明説明（159)V. Invention Description (159)

COOH T L C ： R f 0.22 (己烷：乙酸乙酯=1:1); NM R ： δ 8.15-8.11 (2Η, m), 7.63-7.59 (2H, m), 7.3 (2H, m), 6.92-6.88 (1 H, m), 6.81-6.70 (2H, m), 5.2 (2H, m), 4.29 (2H, s), 4.18-4.02 (1H, m), 2.35 (3H, s), 1.12 (3H, d, J=6.5Hz), 1.04 (3H, d, J=6.5Hz)〇 奮施例2 0 (1 7 ) 4-[2-(N-第三丁基甲基-苯磺醢胺基）-4-甲基苯氧甲基]苯 甲酸COOH TLC: R f 0.22 (hexane: ethyl acetate = 1: 1); NM R: δ 8.15-8.11 (2Η, m), 7.63-7.59 (2H, m), 7.3 (2H, m), 6.92- 6.88 (1 H, m), 6.81-6.70 (2H, m), 5.2 (2H, m), 4.29 (2H, s), 4.18-4.02 (1H, m), 2.35 (3H, s), 1.12 (3H , d, J = 6.5Hz), 1.04 (3H, d, J = 6.5Hz). Example 2 0 (1 7) 4- [2- (N-Third-butylmethyl-benzenesulfonamido)- 4-methylphenoxymethyl] benzoic acid

COOH (請先閱讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

經濟部中央標準局員工消費合作社印製 TLC : R f 0.37 (氯仿：甲醇=9 ·· 1); NMR ： δ 8.08 (2H, d, J=8Hz), 7.55 (2H, m), 7.39 (1 H, m), 7.32-7.20 (4H, m), 7.17 (1 H, d, J=2Hz), 7.03 (1 H, dd, J=8 and 2Hz), 6.68 (1 H, d, J=8Hz), 4.90 (1 H, d, J=13Hz), 4.59 (1 H, d, J=13Hz), 3.57 (1 H, d, J=14Hz)/,3.50 (1H, d, J=14Hz), 2·28 (3H, s), 0.88 (9H, s)。 奮嫵例2 0 ( 1 8 ) 4-[2-(H-異丙基-甲磺酿胺基）-5-三氟甲基笨氧甲基]苯甲 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 159 3933 1 523506 A7 B7Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.37 (chloroform: methanol = 9 ·· 1); NMR: δ 8.08 (2H, d, J = 8Hz), 7.55 (2H, m), 7.39 (1 H, m), 7.32-7.20 (4H, m), 7.17 (1 H, d, J = 2Hz), 7.03 (1 H, dd, J = 8 and 2Hz), 6.68 (1 H, d, J = 8Hz ), 4.90 (1 H, d, J = 13Hz), 4.59 (1 H, d, J = 13Hz), 3.57 (1 H, d, J = 14Hz) /, 3.50 (1H, d, J = 14Hz), 2 · 28 (3H, s), 0.88 (9H, s). Example 2 0 (1 8) 4- [2- (H-isopropyl-methanesulfonylamino) -5-trifluoromethylbenzyloxymethyl] benzyl This paper is in accordance with Chinese national standards ( CNS) A4 size (210X 297 mm) 159 3933 1 523506 A7 B7

〇2s、 五、發明説明（1 6() 酸〇2s, V. Description of the invention (1 6 () acid

COOH TLC : R f 0_32 (氯仿：甲酵=9:1); NMR ：δ 8.17 (2Η, d, J=8.5Hz), 7.58 (2H, d, J=8.5Hz), , 7.43-7.23 (3H, m), 5.20 (2H, s), 4.32 (1H, m), 2.91 (3H, s), 1.29 (3H, d, J=7Hz), 1.10 (3H, d, J=7Hz)〇 g 施例 20 (19) 4-[2-(N-異丙基-乙磺醢胺基）-5-三氟甲基苯氧甲基]苯甲 酸 (請先閲讀背面之注意事項再填寫本頁)COOH TLC: R f 0_32 (chloroform: formazan = 9: 1); NMR: δ 8.17 (2Η, d, J = 8.5Hz), 7.58 (2H, d, J = 8.5Hz),, 7.43-7.23 (3H , m), 5.20 (2H, s), 4.32 (1H, m), 2.91 (3H, s), 1.29 (3H, d, J = 7Hz), 1.10 (3H, d, J = 7Hz) 〇g Example 20 (19) 4- [2- (N-Isopropyl-Ethylsulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 〇2S、/ T L C ： R f 0.36 (氯仿：甲醇= 9:1); NMR ：δ 8.18 (2Η, d, J=8.5Hz), 7.59 (2H, d, J=8.5Hz), , 7.43-7.23 (3H, m), 5.19 (2H, S), 4.33 (1H, m), 3.03 (2H, q, J= 7.5Hz), 1.32-1.17 (6H, m), 1.09 (3H, d, J=7Hz)〇 奮酿例2 0 ( 2 0 ) 4-[2-(N-異丙基-環戊基甲基磺醯胺基）-5-甲基苯氧甲基] 苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 160 3933 1 523506 A7 B7 五、發明説明（161)Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs / TLC: R f 0.36 (chloroform: methanol = 9: 1); NMR: δ 8.18 (2Η, d, J = 8.5Hz), 7.59 (2H, d, J = 8.5Hz),, 7.43-7.23 (3H, m), 5.19 (2H, S), 4.33 (1H, m), 3.03 (2H, q, J = 7.5Hz), 1.32-1.17 (6H, m) , 1.09 (3H, d, J = 7Hz). Exercising example 2 0 (2 0) 4- [2- (N-isopropyl-cyclopentylmethylsulfonamido) -5-methylphenoxy Methyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) 160 3933 1 523506 A7 B7 V. Description of the invention (161)

C〇〇HC〇〇H

NMR ： δ 8.17-8.13 (2H, m), 7.59-7.55 (2H, m), 7.16-7.12 (1H, m), 6.83-6.80 (2H, m), 5.13 (2H’ s), 4.31 (1H, i：峯，J=7Hz)，3.04-3.00 (2H, m), 2.36 (3H，s), 2.4-2.2 (1 H, m), 2.0-1.8 (2H, m), 1.6-1.4 (4H, m ), 1.24 (3H, d, J=7Hz), 1.3-1.1 (2H, m), 1.09 (3H, d, J=7Hz)〇 奮_例？. o f以） 4-[2-(N-環己基甲基-丙磺醢胺基）-5-甲基苯氧甲基]苯甲 酸NMR: δ 8.17-8.13 (2H, m), 7.59-7.55 (2H, m), 7.16-7.12 (1H, m), 6.83-6.80 (2H, m), 5.13 (2H's), 4.31 (1H, i: peak, J = 7Hz), 3.04-3.00 (2H, m), 2.36 (3H, s), 2.4-2.2 (1 H, m), 2.0-1.8 (2H, m), 1.6-1.4 (4H, m), 1.24 (3H, d, J = 7Hz), 1.3-1.1 (2H, m), 1.09 (3H, d, J = 7Hz) o f to) 4- [2- (N-cyclohexylmethyl-propanesulfonylamino) -5-methylphenoxymethyl] benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

經滴部中央標準局員工消費合作社印製 TLC ： R f 0.43 (氯仿：甲醇= 9:1); NM R ： δ 8.1 6 (2H, d, J=8.6Hz), 7.54 (2H, d, J=8.6Hz), 7.26 (1 H, d, J=8.6Hz), 6.9-6.8 (2H, m), 5.17 (2H, s), 3.5-3.4 (2H, m), 2.9-2.8 (2H, m), 2.35 (3H,s), 2.0-1 .〇（13H，m)，0.84 (3H, t, J=8.0Hz), 4.0-1 ·0 (1H，br)。 ' 奮施例20 (22) 4-[2-(N-環戊基甲基-丙磺醵胺基）-5 -甲基苯氧甲基]苯甲 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 161 3933 1Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Transportation TLC: R f 0.43 (chloroform: methanol = 9: 1); NM R: δ 8.1 6 (2H, d, J = 8.6Hz), 7.54 (2H, d, J = 8.6Hz), 7.26 (1 H, d, J = 8.6Hz), 6.9-6.8 (2H, m), 5.17 (2H, s), 3.5-3.4 (2H, m), 2.9-2.8 (2H, m ), 2.35 (3H, s), 2.0-1.〇 (13H, m), 0.84 (3H, t, J = 8.0Hz), 4.0-1 · 0 (1H, br). '' Example 20 (22) 4- [2- (N-Cyclopentylmethyl-propanesulfonylamino) -5 -methylphenoxymethyl] benzoic acid This paper is applicable to Chinese National Standards (CNS) A4 size (210X 297 mm) 161 3933 1

523506 A7 B7 五、發明説明（162!523506 A7 B7 V. Description of the invention (162!

C〇〇H TLC ： R f 0.38 (氛仿：甲醇= 9:1); NMR ： 5 8.16 (2H, d, J=8.4Hz), 7.54 (2H,d, J=8.4Hz), 7.26 (1H, d, J=8.4Hz), 6.9-6.8 (2H, m), 5.17 (2H, s), 3.6-3.5 (2H, m), 2.9-2.8 (2H, m), 2.35 (3H, s), 2.0-1 ·〇 (11H，m)，0.84 (3H, t，J=7.6Hz)，6.0-4.0 (1H, br)。 奮）fe 锎？ (W 2 3 ) (請先閱讀背面之注意事項再填寫本頁) 4-[2-(H-異丙基-丙磺釀胺基）-5-三氟甲基苯氧甲基]桂皮 酸C〇H TLC: R f 0.38 (Fluent: methanol = 9: 1); NMR: 5 8.16 (2H, d, J = 8.4Hz), 7.54 (2H, d, J = 8.4Hz), 7.26 (1H , d, J = 8.4Hz), 6.9-6.8 (2H, m), 5.17 (2H, s), 3.6-3.5 (2H, m), 2.9-2.8 (2H, m), 2.35 (3H, s), 2.0-1 · 〇 (11H, m), 0.84 (3H, t, J = 7.6Hz), 6.0-4.0 (1H, br). Fen) fe? (W 2 3) (Please read the precautions on the back before filling this page) 4- [2- (H-isopropyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid

丁 L C : R f 0.32 (氯仿：甲醇：乙酸=1 〇 〇 : 5 : 1 ); 經濟部中央標準局員工消費合作社印製 NMR ： 5 7.80 (1H,d,J=1 6.2Hz), 7.61 (2H, d, J=8.6Hz), 7.51 (2H,d, J=8.6Hz), 7.39 (1 H, d, J=8.8Hz), 7.24-7.33 (2H, m), 6.49 (1 H, d, J=1 6.2Hz), 5.1 2 (2H, s), 4.31 (1 H, m), 2.95 (2H, m), 1.77 (2H, m), 1.26 (3H, d, J=6.6Hz), 1.09 (3H, d, J=6.6Hz), 0.82 (3H，t, J=7.2Hz)。 y _ 例 20 ( 24) 〈 4-[2-(N-異丙基-戊磺醢胺基）-5-三氟甲基苯氧甲基]桂皮 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 162 3933 1 523506 A7 __ B7 五、發明説明（163)Ding LC: R f 0.32 (chloroform: methanol: acetic acid = 1 00: 5: 1); NMR printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: 5 7.80 (1H, d, J = 1 6.2Hz), 7.61 ( 2H, d, J = 8.6Hz), 7.51 (2H, d, J = 8.6Hz), 7.39 (1 H, d, J = 8.8Hz), 7.24-7.33 (2H, m), 6.49 (1 H, d , J = 1 6.2Hz), 5.1 2 (2H, s), 4.31 (1 H, m), 2.95 (2H, m), 1.77 (2H, m), 1.26 (3H, d, J = 6.6Hz), 1.09 (3H, d, J = 6.6Hz), 0.82 (3H, t, J = 7.2Hz). y _ Example 20 (24) <4- [2- (N-Isopropyl-pentylsulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid This paper applies Chinese national standards (CNS) A4 specifications (210X297 mm) 162 3933 1 523506 A7 __ B7 V. Description of the invention (163)

T L C ： R f 0.27 (氯仿：甲醇：乙酸=100:5:1); NMR ： 5 7.80 (1H,d, J=16.0Hz),7.61 (2H, d, J=8.4Hz), 7.51 (2H,d, J=8.4Hz), 7.39 (1H, m), 7.24-7.33 (2H, m), 6.48 (1 H, d, J=16.0Hz), 5.12 (2H,s),4.31 (1H, sept, J=6.6Hz), 2.96 (2H, m), 1.72 (2H, m), 1.26 (3H, d, J=6.6Hz), 1.05-1.23 (7H, m)，〇.83(3H，t，J=6.2Hz)。 SL施例 20 (25 ) 4-[2-(H-異丙基-2-呋喃基磺醮胺基）-5-三氟甲基笨氧甲 基]笨甲酸TLC: R f 0.27 (chloroform: methanol: acetic acid = 100: 5: 1); NMR: 5 7.80 (1H, d, J = 16.0Hz), 7.61 (2H, d, J = 8.4Hz), 7.51 (2H, d, J = 8.4Hz), 7.39 (1H, m), 7.24-7.33 (2H, m), 6.48 (1 H, d, J = 16.0Hz), 5.12 (2H, s), 4.31 (1H, sept, J = 6.6Hz), 2.96 (2H, m), 1.72 (2H, m), 1.26 (3H, d, J = 6.6Hz), 1.05-1.23 (7H, m), 0.83 (3H, t, J = 6.2Hz). SL Example 20 (25) 4- [2- (H-Isopropyl-2-furylsulfonamido) -5-trifluoromethylbenzyloxymethyl] benzoic acid

^ XOOH (請先閱讀背面之注意事項再填寫本頁)^ XOOH (Please read the notes on the back before filling this page)

〇 NIS 3C 7 〇.〇 NIS 3C 7 〇.

經濟部中央標準局員工消費合作社印製 T L C ： R f 0.22 (己烷：乙酸乙酯=1:1); NMR ：δ8.15 (2H, d,J=8Hz), 7.59 (2H, d, J=8Hz), 7.46 (1H, dd, J=2, 1Hz), 7.23 (3H, m), 6.94 (1 H, dd, J=3.5, 1 Hz), 6.44 (1 H, dd, J=3.5, 2Hz), 5.18 (2H, s), 4.49 (1H, m), 1.10 (6H, dd，J=7, 2.5Hz)。 &lt;、 奮施姻20 (26 ) 4 - [2-(N_異丙基-2-睡吩基磺醢胺基）-5-三氟甲基苯氧甲 基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 公釐） 163 3933 1 523506 Μ Β7 五、發明説明（1 6TLC printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: R f 0.22 (hexane: ethyl acetate = 1: 1); NMR: δ 8.15 (2H, d, J = 8Hz), 7.59 (2H, d, J = 8Hz), 7.46 (1H, dd, J = 2, 1Hz), 7.23 (3H, m), 6.94 (1 H, dd, J = 3.5, 1 Hz), 6.44 (1 H, dd, J = 3.5, 2Hz), 5.18 (2H, s), 4.49 (1H, m), 1.10 (6H, dd, J = 7, 2.5Hz). &lt;, Fen Shi Marriage 20 (26) 4-[2- (N_Isopropyl-2-phenylphensulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid Applicable to paper size China National Standard (CNS) A4 specification (210X mm) 163 3933 1 523506 Μ B7 V. Description of invention (1 6

COOHCOOH

T L C : R f 0.24 (己烷：乙酸乙酯=1:1); NM R ： δ 8.15 (2Η, d, J=8.5Hz), 7.57 (2H, d, J=8.5Hz), 7.54-7.51 (2H, m), 7.25 (3H, m), 7.01-6.99 (1H, m), 5.19 (2H, s), 4.49-4.44 (1H, m), 1.10 (6H, d, J=6.5Hz)〇 實施例2 0 ( 2 7 )4-[2·(Ν-異丙基-4-氯苯磺醣胺基）-5-三氟甲基苯氧甲基] 苯甲酸 ---------— (請先閱讀背面之注意事項再填寫本頁) 訂 經滴部中央標準局員工消費合作社印製TLC: R f 0.24 (hexane: ethyl acetate = 1: 1); NM R: δ 8.15 (2Η, d, J = 8.5Hz), 7.57 (2H, d, J = 8.5Hz), 7.54-7.51 ( 2H, m), 7.25 (3H, m), 7.01-6.99 (1H, m), 5.19 (2H, s), 4.49-4.44 (1H, m), 1.10 (6H, d, J = 6.5Hz) Example 2 0 (2 7) 4- [2 ((N-isopropyl-4-chlorobenzenesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid -------- -— (Please read the notes on the back before filling in this page)

NMR (DMSO-d^) ： 6 7.93 (2H,d,J=8.4Hz), 7.73 (2H,d,J=8.4Hz), 7.56(1 h s), 7.50-7.28 (6H, m), 5.22 (2H, s)，4.38 (1H,七峯，J=6.6Hz), 1·00 (3H, c J=6.6Hz), 0.93 (3H, d, J=6.6Hz)〇 、 奮施例2 0 ( 24-[2-(H-異丙基-4-乙基苯磺醸胺基）-5-三氟甲基苯氧甲 基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 164 3933 1 523506 A7 B7 五、發明説明（165) rrNMR (DMSO-d ^): 6 7.93 (2H, d, J = 8.4Hz), 7.73 (2H, d, J = 8.4Hz), 7.56 (1 hs), 7.50-7.28 (6H, m), 5.22 ( 2H, s), 4.38 (1H, seven peaks, J = 6.6Hz), 1.00 (3H, c J = 6.6Hz), 0.93 (3H, d, J = 6.6Hz), Fenshi 2 0 ( 24- [2- (H-Isopropyl-4-ethylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid The paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 Mm) 164 3933 1 523506 A7 B7 V. Description of the invention (165) rr

C〇〇H T L C ： R f 0.40 (氯仿：甲醇=10:1); NMR (DMSO-d^) ： δ 7.94 (2H, d, J=8.4Hz), 7.66 (2H, d, J=8.4Hz), 7.55 (1 H, d, J=1Hz), 7.49 (2H, d, J=8.4Hz), 7.39 (1H, dd, J=8.4Hz, 1Hz), 7.32 (1H, d, J=8.4Hz), 7·23 (2H，d, J=8.4Hz)，5.25 (2H, s)，4.14 (1 H，七峯，J=6.6Hz), 2.61 (2H, q, J=7.4Hz), 1.14 (3H, t, J=7.4Hz), 1.00 (3H, d, J=6.6Hz), 0.93 (3H, d, J=6.6Hz)〇 g _ 锎 20(29) 4-[2-(N-異丙基-4-丙基苯磺醢胺基）-5-三氟甲基苯氧甲 基]笨甲酸CO〇HTLC: R f 0.40 (chloroform: methanol = 10: 1); NMR (DMSO-d ^): δ 7.94 (2H, d, J = 8.4Hz), 7.66 (2H, d, J = 8.4Hz) , 7.55 (1 H, d, J = 1Hz), 7.49 (2H, d, J = 8.4Hz), 7.39 (1H, dd, J = 8.4Hz, 1Hz), 7.32 (1H, d, J = 8.4Hz) , 7.23 (2H, d, J = 8.4Hz), 5.25 (2H, s), 4.14 (1H, seven peaks, J = 6.6Hz), 2.61 (2H, q, J = 7.4Hz), 1.14 ( 3H, t, J = 7.4Hz), 1.00 (3H, d, J = 6.6Hz), 0.93 (3H, d, J = 6.6Hz) 〇g _ 锎 20 (29) 4- [2- (N-iso Propyl-4-propylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOHCOOH

經滴部中央標準局員工消費合作社印製 NMR (DMSO-d&amp;) ： δ 7.94 (2H, d, J=8.4Hz), 7.65 (2H, d, J=8.4Hz), 7.55 (1 Η, d, J=1Hz), 7.50 (2H, d, J=8.4Hz), 7.39 (1H, dd, J=8.4Hz, 1 Hz), 7.32 (1H, d, J=8_4Hz), 7.20 (2H, d, J=8.4Hz), 5.25 (2H，s), 4.13 (1H，七峯，J=6.6Hz), 2.55 (2H, t, J=7.4Hz), 1.54 (2H, tq, J=7.4Hz, 7.4Hz), 0.97 (3H, d, J=6.6Hz), 0.90 (3H, d, J=6.6Hz)，0.84 (3H, t, J=7.4Hz)。 奮嫵俐2 0 ( 3 0 ) 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨0'乂297公釐） 165 3933 1 523506 kl B7 五、發明説明（166)4-[2-(N-異丙基-4-丁基苯磺酿胺基）-5-三氟甲基苯氧甲 基]苯甲酸NMR (DMSO-d &amp;) printed by the Consumer Cooperative of the Central Bureau of Standards of Didi: δ 7.94 (2H, d, J = 8.4Hz), 7.65 (2H, d, J = 8.4Hz), 7.55 (1 Η, d , J = 1Hz), 7.50 (2H, d, J = 8.4Hz), 7.39 (1H, dd, J = 8.4Hz, 1 Hz), 7.32 (1H, d, J = 8_4Hz), 7.20 (2H, d, J = 8.4Hz), 5.25 (2H, s), 4.13 (1H, seven peaks, J = 6.6Hz), 2.55 (2H, t, J = 7.4Hz), 1.54 (2H, tq, J = 7.4Hz, 7.4 Hz), 0.97 (3H, d, J = 6.6Hz), 0.90 (3H, d, J = 6.6Hz), 0.84 (3H, t, J = 7.4Hz). Fen Li Li 2 0 (3 0) This paper size applies the Chinese National Standard (CNS) A4 specification (2 丨 0 '乂 297 mm) 165 3933 1 523506 kl B7 V. Description of the invention (166) 4- [2- ( N-isopropyl-4-butylbenzenesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid

COOH C4H9 T L C : R f 0.41 (氯仿：甲醇=10:1); NMR (DMSO-db) ： δ 7.94 (2Η, d, J=8.4Hz), 7.65 (2H, d, J=8.4Hz), 7.55 (1 H, d, J=1Hz), 7.49 (2H, d, J=8.4Hz), 7.38 (1H, dd, J=8.4Hz, 1 Hz), 7.33 (1H, d, J=8.4Hz), 7.20 (2H, d, J=8.4Hz), 5.24 (2H, s), 4.14 (1H, t*, J=6.6Hz), 2.57 (2H, t, J=7.4Hz), 1.49 (2H, m), 1.25 (2H, m), 0.98 (3H, d, J=6.6Hz), 0.89 (3H, d, J=6.6Hz)，0.87 (3H, t, J=7.4Hz)〇 (請先閲讀背面之注意事項再填寫本頁) 經滴部中央標準局員工消費合作社印製 g MS 例 21-21(16) 使用2 -硝基酚或對應化合物，依參考例64參考例12 4參考例24實施例2之相同操作，得具下列物理數據之標 題化合物。 鬣 II214-(2-苯磺醯胺基苯氧甲基）苯甲酸 αCOOH C4H9 TLC: R f 0.41 (chloroform: methanol = 10: 1); NMR (DMSO-db): δ 7.94 (2Η, d, J = 8.4Hz), 7.65 (2H, d, J = 8.4Hz), 7.55 (1 H, d, J = 1Hz), 7.49 (2H, d, J = 8.4Hz), 7.38 (1H, dd, J = 8.4Hz, 1 Hz), 7.33 (1H, d, J = 8.4Hz), 7.20 (2H, d, J = 8.4Hz), 5.24 (2H, s), 4.14 (1H, t *, J = 6.6Hz), 2.57 (2H, t, J = 7.4Hz), 1.49 (2H, m) , 1.25 (2H, m), 0.98 (3H, d, J = 6.6Hz), 0.89 (3H, d, J = 6.6Hz), 0.87 (3H, t, J = 7.4Hz) 〇 (Please read the back Note this page, please fill in this page) g MS printed by the Consumer Standards Cooperative of the Central Bureau of Standards. Example 21-21 (16) Use 2-nitrophenol or corresponding compound according to Reference Example 64 Reference Example 12 4 Reference Example 24 Example By the same operation as in 2, the title compound having the following physical data was obtained. Iguana II214- (2-benzenesulfonamidophenoxymethyl) benzoic acid α

NH 02SNH 02S

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）This paper size applies to China National Standard (CNS) A4 (210X 297 mm)

COOH 166 3 933 1 523506 A7 B7 五、發明説明（1 67) T L C : R f 0.35 (乙酸乙酯：己烷：乙醭= 6:13:1); (請先閲讀背面之注意事項再填寫本頁) NMR (DMSO-d^) ：δ 12.86 (1H, brs), 9.53 (1H, brs), 7.91 (2H, d, J=8.0Hz), 7.66 (2H, d, J=8.0Hz), 7.52 (1H, t, J=7.0Hz), 7.45-7.25 (5H, m), 7.08 (1H, t, J=9.0Hz), 6.95-6.80 (2H，m)，4.91 (2H, s)〇 奮_例21 (1 ) 4-[2-(4-氯苯磺釀胺基）苯氧甲基]苯甲酸COOH 166 3 933 1 523506 A7 B7 V. Description of the invention (1 67) TLC: R f 0.35 (ethyl acetate: hexane: acetamidine = 6: 13: 1); (Please read the notes on the back before filling in this Page) NMR (DMSO-d ^): δ 12.86 (1H, brs), 9.53 (1H, brs), 7.91 (2H, d, J = 8.0Hz), 7.66 (2H, d, J = 8.0Hz), 7.52 (1H, t, J = 7.0Hz), 7.45-7.25 (5H, m), 7.08 (1H, t, J = 9.0Hz), 6.95-6.80 (2H, m), 4.91 (2H, s) Example 21 (1) 4- [2- (4-chlorobenzenesulfonylamino) phenoxymethyl] benzoic acid

^ /C〇〇H^ / C〇〇H

NMR (DMSO-dfc) -： δ 12.85 (1 H, brs), 9.68 (1H, brs), 7.93 (2H, d, J=8.5Hz), 7.60 (2H, d, J=8.5Hz), 7.36 (4H, d, J=8.5Hz), 7.35-7.25 (1H, m), 7.12 (1H, dt, J=7.5, 2.0Hz)，6.96-6.85 (2H, m), 4·92 (2H，s)。 奮_例2 ΐ ( 2 ) 4-(2-苯磺醢胺基-4-氟苯氧甲基）笨甲酸 經濟部中央標準局員工消費合作社印製NMR (DMSO-dfc)-: δ 12.85 (1 H, brs), 9.68 (1H, brs), 7.93 (2H, d, J = 8.5Hz), 7.60 (2H, d, J = 8.5Hz), 7.36 ( 4H, d, J = 8.5Hz), 7.35-7.25 (1H, m), 7.12 (1H, dt, J = 7.5, 2.0Hz), 6.96-6.85 (2H, m), 4.92 (2H, s) . Fen_Example 2 ΐ (2) 4- (2-benzenesulfonamido-4-fluorophenoxymethyl) benzic acid Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

02S02S

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐）This paper size applies to China National Standard (CNS) A4 (210X 297 mm)

C〇〇H 167 3933 1 523506 A7 B7 五、發明説明（168) T L C : R f 0.37 (乙酸乙酯：己烷：乙酸= 6:13:1); (請先閲讀背面之注意事項再填寫本頁) NMR (DMS〇-d6) :δ 12.95 (1 H, brs), 9.90 (1 H, brs), 7.90 (2H, d, J=8.5Hz), 7.72 (2H, d, J=7.0Hz), 7.58 (1H, m), 7.46 (2H, t, J=7.5Hz), 7.37 (2H, d, J=8.5Hz), 7.10 (1H，d, J=9.5Hz), 6.92 (2H，d, J=7.0Hz), 4.95 (2H，s)。 奮_例(m 4-(2-苯磺醢胺基-5-氟苯氧甲基）苯甲酸C〇H 167 3933 1 523506 A7 B7 V. Description of the invention (168) TLC: R f 0.37 (ethyl acetate: hexane: acetic acid = 6: 13: 1); (Please read the precautions on the back before filling in this Page) NMR (DMS〇-d6): δ 12.95 (1 H, brs), 9.90 (1 H, brs), 7.90 (2H, d, J = 8.5Hz), 7.72 (2H, d, J = 7.0Hz) , 7.58 (1H, m), 7.46 (2H, t, J = 7.5Hz), 7.37 (2H, d, J = 8.5Hz), 7.10 (1H, d, J = 9.5Hz), 6.92 (2H, d, J = 7.0Hz), 4.95 (2H, s). Fen_Example (m 4- (2-benzenesulfonamido-5-fluorophenoxymethyl) benzoic acid

八 XOOHEight XOOH

T L C ： R f 0.42 (乙酸乙酯：己烷：乙酸= 6:13:1); NMR (DMSO-dfe) :δ 12.95 (1 H, brs), 9.65 (1H, brs), 7.91 (2H, d, J=8.5Hz), 7.60 (2H, d, J=7.0Hz), 7.52 (1 H, t, J=7.0Hz), 7.39 (2H, d, J=7.5Hz), 7.35 (2H, d, J=7.5Hz), 7.26 (1H, dd, J=7.0,6.5Hz), 6.84 (1H, dd, J=11.0, 2.5Hz), 6.75 (1H, dt, J=8.5, 2.5Hz), 4.90 (2H, s)。 啻牖例21 U) 4-(2 -苯磺醢胺基-4 -溴苯氧甲基）苯甲酸 經濟部中央標準局員工消費合作社印tTLC: R f 0.42 (ethyl acetate: hexane: acetic acid = 6: 13: 1); NMR (DMSO-dfe): δ 12.95 (1 H, brs), 9.65 (1H, brs), 7.91 (2H, d , J = 8.5Hz), 7.60 (2H, d, J = 7.0Hz), 7.52 (1 H, t, J = 7.0Hz), 7.39 (2H, d, J = 7.5Hz), 7.35 (2H, d, J = 7.5Hz), 7.26 (1H, dd, J = 7.0, 6.5Hz), 6.84 (1H, dd, J = 11.0, 2.5Hz), 6.75 (1H, dt, J = 8.5, 2.5Hz), 4.90 ( 2H, s). Example 21 U) 4- (2-Benzosulfenylamino-4-bromophenoxymethyl) benzoic acid Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

COOHCOOH

XXXX

Br 'NHo2s 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 168 39 3 3 1 523506 A7 B7 五、發明説明（169) T L C : R f 0.25 (乙酸乙酯：己烷：乙酸= 6:13:1); NMR (DMSO-d6) ：δ 12.97 (1Η, brs), 9.97 (1H, brs), 7.90 (2H, d, J=8.0Hz), 7.69 (2H, dd, J=7.5, 2Hz), 7.58 (1 H, tt, J=7.5, 2Hz), 7.46 (2H, d, J=7.5Hz), 7.39 (1 H, d, J=2.5Hz), 7.36 (2H, d, J=8.0Hz), 7.27 (1 H, dd, J=9.0, 2.5Hz), 6.89 (1 H, d, J=9Hz), 4.97 (2H，s)。 奮）fe 例？· 1 f s) 4-(2-苯磺醯胺基-5-氯苯硫甲基）苯甲酸Br 'NHo2s This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) 168 39 3 3 1 523506 A7 B7 V. Description of the invention (169) TLC: R f 0.25 (ethyl acetate: hexane: acetic acid = 6: 13: 1); NMR (DMSO-d6): δ 12.97 (1Η, brs), 9.97 (1H, brs), 7.90 (2H, d, J = 8.0Hz), 7.69 (2H, dd, J = 7.5 , 2Hz), 7.58 (1 H, tt, J = 7.5, 2Hz), 7.46 (2H, d, J = 7.5Hz), 7.39 (1 H, d, J = 2.5Hz), 7.36 (2H, d, J = 8.0Hz), 7.27 (1 H, dd, J = 9.0, 2.5Hz), 6.89 (1 H, d, J = 9Hz), 4.97 (2H, s). Fen) fe case? · 1 f s) 4- (2-benzenesulfonamido-5-chlorophenylthiomethyl) benzoic acid

ClCl

OC sjaOC sja

C〇〇H (請先閱讀背面之注意事項再填寫本頁)C〇〇H (Please read the notes on the back before filling this page)

NH 02S TLC ： R f 0.50 (氯仿：甲醇：乙酸= l〇〇:5:l); NMR ：δ 7.99 (2H, d, J=8.4Hz), 7.78 (2H, m), 7.41-7.62 (5H, m), 7.23 (1H, dd, J=2.6, 8.8Hz)，7.08 (1H, d，J=2.6Hz), 7.05 (2H, d，J=8.6Hz)，3·71 (2H, s)。 奮）fe 例 (fn 4-(2-苯磺醢胺基-4-甲氧基苯氧甲基）苯甲酸 經濟部中央標準局員工消費合作社印tNH 02S TLC: R f 0.50 (chloroform: methanol: acetic acid = 100: 5: l); NMR: δ 7.99 (2H, d, J = 8.4Hz), 7.78 (2H, m), 7.41-7.62 (5H , m), 7.23 (1H, dd, J = 2.6, 8.8Hz), 7.08 (1H, d, J = 2.6Hz), 7.05 (2H, d, J = 8.6Hz), 3.71 (2H, s) . Fen) fe case (fn 4- (2-benzenesulfonamido-4-methoxyphenoxymethyl) benzoic acid Employee Consumer Cooperative Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

JOC jaJOC ja

COOHCOOH

MeO&quot; NH 02S X) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 169 3933 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（170) T L C ： R f 0.38 (氯仿：甲醇=17:3); NMR (DMSO-d6) ：δ 7.90 (2Η, d, J=8.5Hz), 7.71 (2H, d, J=8.0Hz), 7.64-7.35 (5H, m), 6.90-6·80 (2H, m)，6.44 (1 H, dd, J=9.0 及 3.〇Hz), 4.89 (2 H, s), 3.65 (3 H, m)〇 實施例2 1 ( 7 ) 4- (2-苯磺醢胺基 氟甲基苯氧甲基）苯甲酸MeO &quot; NH 02S X) This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 169 3933 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (170) TLC: R f 0.38 (chloroform: methanol = 17: 3); NMR (DMSO-d6): δ 7.90 (2Η, d, J = 8.5Hz), 7.71 (2H, d, J = 8.0Hz), 7.64-7.35 (5H, m), 6.90-6 · 80 (2H, m), 6.44 (1 H, dd, J = 9.0 and 3.0 Hz), 4.89 (2 H, s), 3.65 (3 H, m). Example 2 1 (7) 4- (2-benzenesulfonamidofluoromethylphenoxymethyl) benzoic acid

F3CT v 、NH 〇2SF3CT v, NH 〇2S

C〇〇H T L C : R f 0.32 (氯仿：甲醇=17:3); NMR (DMSO-d&amp;) ：δ 7.92 (2H, d, J=8.5Hz), 7.69 (2H, d, J=8.0Hz), 7.63-7.34 (7H，m)，7.11 (1H，d, J=8.5Hz), 5_09 (2H, s)。 管_例21 f S) 4-(2-苯磺醢胺基-4-甲基笨氧甲基）笨甲酸C〇HTLC: R f 0.32 (chloroform: methanol = 17: 3); NMR (DMSO-d &amp;): δ 7.92 (2H, d, J = 8.5Hz), 7.69 (2H, d, J = 8.0Hz) , 7.63-7.34 (7H, m), 7.11 (1H, d, J = 8.5Hz), 5_09 (2H, s). Example 21 f S) 4- (2-benzenesulfonamido-4-methylbenzyloxymethyl) benzate

C〇〇H (請先閱讀背面之注意事項再填寫本頁)C〇〇H (Please read the notes on the back before filling this page)

NH 〇2S T L C : R f 0.43 (乙酸乙酯：己燒：乙酸=7 : 1 2 : 1); NMR (DMSO-dfe) ：δ 7.89 (2H, d, J=8.0Hz), 7.66 (2H, d, J=7.0Hz), 7.60-7.48 (1 H, m), 7.41 (2H, d, J=8.0Hz), 7.35 (2H, d, J=8Hz), 7.11 (1 H, d, J=2.0Hz), 6.90 (1H, dd, J=8.0, 2·0Ηζ), 6.76 (1H, d，J=8Hz), 4.88 (2H, s), 2_19 (3H, s)。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 170 3933 1 523506 A7 _____ B7 五、發明説明（171) 置Μ例2 1 ( Q、 4-(2-苯磺醢胺基-5 -甲基苯氧甲基）苯甲酸 經濟部中央標準局員工消費合作社印製NH 〇2S TLC: R f 0.43 (ethyl acetate: hexane: acetic acid = 7: 1 2: 1); NMR (DMSO-dfe): δ 7.89 (2H, d, J = 8.0Hz), 7.66 (2H, d, J = 7.0Hz), 7.60-7.48 (1 H, m), 7.41 (2H, d, J = 8.0Hz), 7.35 (2H, d, J = 8Hz), 7.11 (1 H, d, J = 2.0Hz), 6.90 (1H, dd, J = 8.0, 2.00Ηζ), 6.76 (1H, d, J = 8Hz), 4.88 (2H, s), 2_19 (3H, s). This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 170 3933 1 523506 A7 _____ B7 V. Description of the invention (171) Example M 2 1 (Q, 4- (2-benzenesulfonamido- 5-Methylphenoxymethyl) benzoic acid Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

T L C ： R f 0.43 (乙酸乙酯：己烷：乙酸=7:12:1); NMR (DMSO-d^ ：δ 7.91 (2Η, d, J=8.5Hz), 7.62 (2H, d, J=7.0Hz), 7.57-7.45 (1H, m), 7.44-7.30 (4H, m), 7.14 (1H, d, J=8.0Hz), 6.75 (1H, s), 6.71 (1H, d, J=8.0Hz), 4.88 (2H, s), 2·21 (3H, s)。 置旛例2 1 f 1 (Π 4-(2 -苄基磺醢胺基-5 -氯苯氧甲基）苯甲酸TLC: R f 0.43 (ethyl acetate: hexane: acetic acid = 7: 12: 1); NMR (DMSO-d ^: δ 7.91 (2Η, d, J = 8.5Hz), 7.62 (2H, d, J = 7.0Hz), 7.57-7.45 (1H, m), 7.44-7.30 (4H, m), 7.14 (1H, d, J = 8.0Hz), 6.75 (1H, s), 6.71 (1H, d, J = 8.0 Hz), 4.88 (2H, s), 2.21 (3H, s). Example 2 1 f 1 (Π 4- (2-benzylsulfonamido-5 -chlorophenoxymethyl) benzoic acid

COOH (請先閲讀背面之注意事項再填寫本頁)COOH (Please read the notes on the back before filling this page)

CI 〇 υιCI 〇 υι

NHNH

〇2S〇2S

丁 L C : R f 0.52 (氯仿：甲酵：乙酸=100: 5:1); NM R (DMSO-dfe) ： δ 7.96 (2H, d, J=8.0Hz), 7.67 (2H, d, J=8.0Hz), 7.29 (5H, &lt;、 s), 7.21 (1 H, d, J=8.2Hz), 7.20 (1 H, d, J=2.4Hz), 6.95 (1 H, dd, J=2.4, 8.2Hz), 5.31 (2H, s), 4·38 (2H, s)。 實施例2 1 (1 4-(2 -苯磺釀胺基-5 -甲氧基苯氧甲基）苯甲酸 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） 171 3933 1 523506 A7 B7DLC: R f 0.52 (chloroform: formazan: acetic acid = 100: 5: 1); NM R (DMSO-dfe): δ 7.96 (2H, d, J = 8.0Hz), 7.67 (2H, d, J = 8.0Hz), 7.29 (5H, &lt;, s), 7.21 (1 H, d, J = 8.2Hz), 7.20 (1 H, d, J = 2.4Hz), 6.95 (1 H, dd, J = 2.4 , 8.2Hz), 5.31 (2H, s), 4.38 (2H, s). Example 2 1 (1 4- (2-benzenesulfonylamino-5 -methoxyphenoxymethyl) benzoic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210 × 297 mm) 171 3933 1 523506 A7 B7

五、發明説明（17V. Description of the invention (17

COOH T L C : R f 0.40 (氯仿：甲酵=4:1); NM R (DMSO-dfe) ： δ 7.90 (2Η, d, J=8.5Hz), 7.59 (2H, d, J=8Hz), 7.51 (1H, t, J=8Hz), 7.44-7.28 (4H, m), 7.1 5 (1 H, d, J=8.5Hz), 6.54-6.47 (2H, m), 4.86 (2H, s)，3·69 (3H, s)。 實施例2 1 (1 2 ) 3-(2-苯磺醯胺基-5-氛苯氧甲基）苯甲酸 (請先閱讀背面之注意事項再填寫本頁)COOH TLC: R f 0.40 (chloroform: formazan = 4: 1); NM R (DMSO-dfe): δ 7.90 (2Η, d, J = 8.5Hz), 7.59 (2H, d, J = 8Hz), 7.51 (1H, t, J = 8Hz), 7.44-7.28 (4H, m), 7.1 5 (1 H, d, J = 8.5Hz), 6.54-6.47 (2H, m), 4.86 (2H, s), 3 · 69 (3H, s). Example 2 1 (1 2) 3- (2-benzenesulfonamido-5-fluorophenoxymethyl) benzoic acid (Please read the precautions on the back before filling this page)

經濟、邺中央標準局員工消費合作社印製 NMR (DMS〇-d6) :δ 13.03 (1H, brs), 9.80 (1H, brs), 7.98 (1H, s), 7.95-7.86 (1H, m), 7.66 (2H, d, J=7.0Hz), 7.58-7.46 (3H, m), 7.40 (2H, t, J=7.0Hz), 7.27 (1 H, d, J=8.5Hz), 7.07 (1 H, d, J=2.5Hz), 6.96 (1 H, dd, J=8.5, 2.5Hz), 4.96 (2H, s)。 （ 管淪例2 1 ( 1 3) 4-(2-苯磺醢胺基-4-氯-5 -甲基苯氧甲基）苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 172 3933 1 523506 A7 B7 五、發明説明（1 73)NMR (DMS〇-d6) printed by the Economic and Social Central Bureau Staff Consumer Cooperative: δ 13.03 (1H, brs), 9.80 (1H, brs), 7.98 (1H, s), 7.95-7.86 (1H, m), 7.66 (2H, d, J = 7.0Hz), 7.58-7.46 (3H, m), 7.40 (2H, t, J = 7.0Hz), 7.27 (1 H, d, J = 8.5Hz), 7.07 (1 H , d, J = 2.5Hz), 6.96 (1 H, dd, J = 8.5, 2.5Hz), 4.96 (2H, s). (Pipeline example 2 1 (1 3) 4- (2-benzenesulfonamido-4-chloro-5 -methylphenoxymethyl) benzoic acid The paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 172 3933 1 523506 A7 B7 V. Description of the invention (1 73)

MeMe

ClCl

T L C ： R f 0.44 (氯仿：甲酵= 4:1); NMR (DMSO-d^) ：δ 7.91 (2Η, d, J=8Hz), 7.66 (2Η, d, J=7Hz), 7.55 (1H, t, J=7.5Hz), 7.47-7.30 (4H, m)} 7.25 (1 H, s), 6.98 (1 H, s), 4.93 (2H, s), 2.23 (3H, s)〇 奮施例21 (1 A) (請先閱讀背面之注意事項再填寫本頁) 4-(2-苯磺醢胺基-4,5-二氯苯氧甲基）苯甲酸TLC: R f 0.44 (chloroform: formazan = 4: 1); NMR (DMSO-d ^): δ 7.91 (2Η, d, J = 8Hz), 7.66 (2Η, d, J = 7Hz), 7.55 (1H , t, J = 7.5Hz), 7.47-7.30 (4H, m)} 7.25 (1 H, s), 6.98 (1 H, s), 4.93 (2H, s), 2.23 (3H, s) Example 21 (1 A) (Please read the precautions on the back before filling out this page) 4- (2-benzenesulfonamido-4,5-dichlorophenoxymethyl) benzoic acid

TLC : R f 0.42 (氯仿：甲醇=4:1); 經濟部中央標準局員工消費合作社印製 NMR (DMSO-dfe) ： 5 7.92 (2H, d, J=8Hz), 7.69 (2H, d, J=7.5Hz), 7.58 (1H, t, J=7.5Hz), 7.50-7.31 (5 H, m), 7.26 (1H, s), 5·01 (2H, s)。 奮 _ 例 2 ΐ η 、 4-(2-苯磺醢胺基-5-氯苯氧甲基）苯二甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 173 3 9 33 1 523506 A7 B7 五、發明説明（174)TLC: R f 0.42 (chloroform: methanol = 4: 1); NMR (DMSO-dfe) printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs: 5 7.92 (2H, d, J = 8Hz), 7.69 (2H, d, J = 7.5Hz), 7.58 (1H, t, J = 7.5Hz), 7.50-7.31 (5 H, m), 7.26 (1H, s), 5.01 (2H, s). Fen_ Example 2 ΐ η, 4- (2-benzenesulfonamido-5-chlorophenoxymethyl) phthalic acid The paper size is applicable to China National Standard (CNS) A4 (210X 297 mm) 173 3 9 33 1 523506 A7 B7 V. Description of the invention (174)

CICI

OC ΧίOC Χί

COOHCOOH

COOHCOOH

ΝΗ 02S X) 丁 L C : R f 0.36 (氯仿：甲醇：乙酸=15:4:1); NMR (DMSO-d^) ： δ 13.23 (2Η, brs), 9.86 (1 H, s), 7.74-7.58 (4H, m), 7.56-7.30 (4H, m), 7.29 (1 H, d, J=8.5Hz), 7.06 (1 H, d, J=2.〇Hz), 6.98 (1 H, dd, J=8.5, 2Hz),4.94 (2H,s)〇 奮施例2 1 f 1 iU4-(2-笨磺醢胺基-5-氯苯氧基）苯甲酸ΝΗ 02S X) DLC: R f 0.36 (chloroform: methanol: acetic acid = 15: 4: 1); NMR (DMSO-d ^): δ 13.23 (2Η, brs), 9.86 (1 H, s), 7.74- 7.58 (4H, m), 7.56-7.30 (4H, m), 7.29 (1 H, d, J = 8.5Hz), 7.06 (1 H, d, J = 2.0 Hz), 6.98 (1 H, dd , J = 8.5, 2Hz), 4.94 (2H, s). Example 2 1 f 1 iU4- (2-benzylsulfonylamino-5-chlorophenoxy) benzoic acid

Cl O' -〇rCl O '-〇r

COOH (請先閲讀背面之注意事項再填寫本頁) NH o2s τ L C ： R f 0.46 (氯仿··甲醇=9:1); 經濟部中央標準局員工消費合作社印製 NM R ； δ 7.99 (2H, d, J=9.0Hz), 7.8-7.7 (3H, m), 7.6-7.5 (1 H, m), 7.5-7.3 (2H, m), 7.15(1 H, dd, J=2.2, 8.8Hz), 6.97 (1 H, s), 6.77 (1 H, d, J=2.2Hz), 6.65 (2H, d, J=9.0Hz)〇COOH (Please read the precautions on the back before filling this page) NH o2s τ LC: R f 0.46 (chloroform ·· methanol = 9: 1); NM R printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs; δ 7.99 (2H , d, J = 9.0Hz), 7.8-7.7 (3H, m), 7.6-7.5 (1 H, m), 7.5-7.3 (2H, m), 7.15 (1 H, dd, J = 2.2, 8.8Hz ), 6.97 (1 H, s), 6.77 (1 H, d, J = 2.2Hz), 6.65 (2H, d, J = 9.0Hz).

參皇eLlA 40(2-硝基氯苯氧基）丙基]苯甲酸甲酯 (a)0H體 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 174 39331 523506 A7 B7 五、發明説明（176) 4-[3-(2 -苯磺醯胺基-5 -氯苯氧基）丙基]苯甲酸Sanhuang eLlA 40 (2-nitrochlorophenoxy) propyl] benzoic acid methyl ester (a) 0H This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) 174 39331 523506 A7 B7 V. DESCRIPTION OF THE INVENTION (176) 4- [3- (2- (benzenesulfenamido-5-chlorophenoxy) propyl] benzoic acid

CICI

OCOC

COOHCOOH

NH 02SNH 02S

使用4-[3-(2-硝基-5-氯苯氧基）丙基]苯甲酸甲酿（由 參考例1 8合成），依參考例1 2 4參考例2 實施例2之相同 操作，得具下列物理數據之標題化合物。 TLC: Rf 0.41(氯仿••甲酵·•乙酸=100:5:1); NMR: 38.04(2H，d,J = 8.4Hz), 7·73(2Η,πι), 7·50(2Η,η〇, 7.40(2H,m), 7.21(2H,d,J=8.2Hz), 5.92(lH,brs), 6.91 (lH,dd,J = 2.2,8.6Hz), 6·67(1Η,υ = 2·2Ηζ), 3·75(2Η, t,J=6.2Hz), 2.70(2H,t,J=7.0Hz), l-98(2H,m) 管 _ 例 22 (Ί ) -22 U) (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 或 酯 半 、 例物 酯考合 乙參化 二-&gt;題 之12標 應例之 對考據 用參數 使分理 18物 例列 2 之 2 例 施 實 酸作 甲操 笨同 基相 醯 乙 考下 參具 依得 例 啻 反 酸 甲 烷 a 環 基 甲 氧 笨 氯 - 5 - 基 胺 釀 磺 笨 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 176 39 3 3 1 523506 A7 B7 五、發明説明（1 7 7)Using 4- [3- (2-nitro-5-chlorophenoxy) propyl] benzoic acid methyl ester (synthesized from Reference Example 18), follow the same operation as Reference Example 1 2 4 Reference Example 2 and Example 2 The title compound has the following physical data. TLC: Rf 0.41 (chloroform • formazan • acetic acid = 100: 5: 1); NMR: 38.04 (2H, d, J = 8.4Hz), 7.73 (2Η, π), 7.50 (2Η, η〇, 7.40 (2H, m), 7.21 (2H, d, J = 8.2Hz), 5.92 (lH, brs), 6.91 (lH, dd, J = 2.2,8.6Hz), 6.67 (1Η, υ = 2 · 2Ηζ), 3.75 (2Η, t, J = 6.2Hz), 2.70 (2H, t, J = 7.0Hz), l-98 (2H, m) tube_ Example 22 (Ί) -22 U ) (Please read the notes on the back before filling out this page) Printed or printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs or the ester half, the sample ester test and the second test of the second standard of &gt; &gt; Questions for the test case 12 The parameters make it possible to divide 18 examples of cases 2 of 2 examples of the use of acid as the base phase of the same operation, the reference is based on the reference example, the acid acid methane a cyclomethylmethoxybenzyl chloride-5-amine sulfonated This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 176 39 3 3 1 523506 A7 B7 V. Description of the invention (1 7 7)

XOOH CK /〇XOOH CK / 〇

NM R ： δ 7.70 (2Η, m), 7.36-7.59 (4H, m), 6.92 (1 H, brs), 6.91 (1 H, dd, J=2.2, 8.4Hz), 6.70 (1H, d, J=2.2Hz), 3.55 (2H, d, J=6.2Hz), 2.31 (1H, tt, J=3.8, 12.0Hz), 2.00-2.19 (2H, m), 1.35-1.85 (5H, m), 0.95 (2H, m)〇 奮 _ 例 2 2 f 順-4-(2-苯磺醢胺基-5-氯苯氧甲基）環己烷甲酸NM R: δ 7.70 (2Η, m), 7.36-7.59 (4H, m), 6.92 (1 H, brs), 6.91 (1 H, dd, J = 2.2, 8.4Hz), 6.70 (1H, d, J = 2.2Hz), 3.55 (2H, d, J = 6.2Hz), 2.31 (1H, tt, J = 3.8, 12.0Hz), 2.00-2.19 (2H, m), 1.35-1.85 (5H, m), 0.95 (2H, m). Example 2 2 f cis-4- (2-benzenesulfonamido-5-chlorophenoxymethyl) cyclohexanecarboxylic acid

^\^COOH^ \ ^ COOH

T L C ： R f 0.53 (氛仿：甲醇：乙酸=100:5:1); 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) NMR ：δ 7.70 (2H, m), 7.35-7.57 (4H, m), 6.89 (1 H, dd, J=2.2, 8.6Hz), 6.84 (1 H, brs), 6.69 (1 H, d, J=2.2Hz), 3.58 (2H, d, J=6.4Hz), 2.70 (1 H, m), 1.98-2.15 (2H, m), 1.43-1.80 (5H, m), 1.15-1.40 (2H, m)〇 &lt;TLC: R f 0.53 (mfm: methanol: acetic acid = 100: 5: 1); printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) NMR: δ 7.70 (2H, m), 7.35-7.57 (4H, m), 6.89 (1 H, dd, J = 2.2, 8.6Hz), 6.84 (1 H, brs), 6.69 (1 H, d, J = 2.2Hz), 3.58 ( 2H, d, J = 6.4Hz), 2.70 (1 H, m), 1.98-2.15 (2H, m), 1.43-1.80 (5H, m), 1.15-1.40 (2H, m) 〇 &lt;

奮）fe例2 2 f W 6-(2-苯磺醢胺-5-氯笨氧甲基）煙鐮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 177 3933 1 523506 A7 B7 五、發明説明（179) ^^N〇2 2-硝基-5-三氟甲基酚（400祖g)之DMF(4.0al)溶液中， 在氩氣流及01C下，添加氫化納（77ag),攪拌30分鐘後， 滴加甲氧甲基氯（147μ1)後攪拌20分鐘。反應混合物Μ冰 水處理，Μ乙酸乙酯萃取。乙酸乙酯層予Μ洗淨、乾燥及 及減壓濃縮，殘留物Κ矽膠管柱層析法（己烷：乙酸乙酯= 20:1)純化，得具下列物理數據之標題化合物（353mg)。 TLC: Rf 0.44(己烷：乙酸乙 _= 10:1)。 參者例20 2-胺基-5-三氟甲基苯基甲氧甲基醚 O^OMe ^^nh2 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2-硝基-5-三氟甲基笨基甲氧甲基醚（353ag,由參考 例1 9合成）之甲醇（3 · 5 π» 1 )溶液中，在氩氣流下添加1 0 %鈀 -碳（30mg),容器內充入氫氣在室溫下激烈攪拌。反應混 合物K矽藻土過濾、減壓濃縮，得具下列物理數據之標題 化合物（3 1 3 ro g )。 、 TLC: Rf 0.44(己烷：乙酸乙 _= 3:1)。 參者例21 N-(2 -甲氧甲氧基-4-三氟甲基苯基）苯磺醯胺基乙酸甲酯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 179 3933 1 523506 A7 B7 五、發明説明（！ 80)Fen) fe case 2 2 f W 6- (2-benzenesulfonamide-5-chlorobenzyloxymethyl) nicotinic acid The paper size is applicable to Chinese National Standard (CNS) A4 specification (210X297 mm) 177 3933 1 523506 A7 B7 V. Description of the invention (179) ^^ NO2 2-nitro-5-trifluoromethylphenol (400 g) in DMF (4.0al) solution, under the flow of argon and 01C, sodium hydride was added (77ag), and after stirring for 30 minutes, methoxymethyl chloride (147 μ1) was added dropwise, followed by stirring for 20 minutes. The reaction mixture was treated with ice and water, and extracted with ethyl acetate. The ethyl acetate layer was washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1) to obtain the title compound (353 mg) with the following physical data. . TLC: Rf 0.44 (hexane: ethyl acetate _ = 10: 1). Participant Example 20 2-Amino-5-trifluoromethylphenylmethoxymethyl ether O ^ OMe ^^ nh2 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling out this page ) In a solution of 2-nitro-5-trifluoromethylbenzyl methoxymethyl ether (353ag, synthesized from Reference Example 19) in methanol (3 · 5 π »1), add 10% under argon flow. Palladium-carbon (30mg), the container was filled with hydrogen and stirred vigorously at room temperature. The reaction mixture K was filtered and concentrated under reduced pressure to obtain the title compound (3 1 3 g) having the following physical data. , TLC: Rf 0.44 (hexane: ethyl acetate _ = 3: 1). Participant Example 21 N- (2-methoxymethoxy-4-trifluoromethylphenyl) benzenesulfonamidomethyl acetate This paper size is applicable to China National Standard (CNS) A4 (210X 297 mm) 179 3933 1 523506 A7 B7 V. Description of the invention (! 80)

XX .O^OMe 'N^COOMeXX .O ^ OMe 'N ^ COOMe

參考例20合成），依參考例2-&gt;實施例17之相同操作，得具 下列物理數據之標題化合物（625ing)。 TLC: Rf 0.66(笨：丙 _ = 9:1)。 參者例22 1,1-二甲基-2-[N-(2-甲氧甲氧基-4-三氟甲基笨基）苯磺 藤胺基]乙醇 F3C(Synthesis of Reference Example 20) According to the same procedure as in Reference Example 2- &gt; Example 17, the title compound (625ing) having the following physical data was obtained. TLC: Rf 0.66 (Stupid: C _ = 9: 1). Reference Example 22 1,1-Dimethyl-2- [N- (2-methoxymethoxy-4-trifluoromethylbenzyl) benzenesulfonylmethyl] ethanol F3C

(請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 N-(2-甲氧甲氧基-4-三氟甲基苯基）苯磺醢胺基乙酸 甲酯（ 5 2 5mg;由參考例21合成）；THF(6.0di1)溶液中，在 氩氣流及0 t!下，滴加溴化甲基鎂（2 . 6 7 m l ),攪拌3 0分鐘 。反應混合物Μ冰水處理，Μ乙酸乙酯萃取，洗淨、乾燥 、減壓濃縮，殘留物Κ矽膠管柱層析法（己烷：乙酸乙酯= 2:1)純化，得具下列物理數據之標題化合物（380mg)。 TLC: Rf 0.26(己烷：乙酸乙酯=2:1) 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 180 393 3 1 523506 A7 五、發明説明（181) 參者例23 1,1-二甲基-2-[N-(2-羥基-4-三氟甲基苯基）苯磺醯胺基） 乙醇(Please read the notes on the back before filling out this page) N- (2-methoxymethoxy-4-trifluoromethylphenyl) benzenesulfonylaminoacetate printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs Esters (5 2 5mg; synthesized from Reference Example 21); In a THF (6.0di1) solution, methyl magnesium bromide (2.67 ml) was added dropwise under a stream of argon and 0 t !, and stirred for 30 minutes. The reaction mixture was treated with ice water, extracted with ethyl acetate, washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain the following physical data. The title compound (380 mg). TLC: Rf 0.26 (hexane: ethyl acetate = 2: 1) The paper size is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 180 393 3 1 523506 A7 V. Description of the invention (181) Participants Example 23 1,1-Dimethyl-2- [N- (2-hydroxy-4-trifluoromethylphenyl) benzenesulfonamido) ethanol

1,1-二甲基-2-[N-(2-甲氧甲氧基-4-三氟甲基苯基） 苯磺釀胺基]乙醇（380mg;由參考例22合成）之THF(4.0ml) 溶液中，添加6N塩酸（0.8al),室溫下攪拌2天。反應混合 物Μ乙酸乙酯稀釋，洗淨、乾燥及減壓濃縮，殘留物Μ矽 膠管柱層析法（己烷：乙酸乙酯=2:1)純化，得具下列物理 數據之標題化合物（291mg)。 TLC : Rf 0 · 29 (苯：丙嗣=9 : 1) 參者例24 — (請先閱讀背面之注意事項再填寫本頁) 訂 基 胺 醯 磺 苯 嫌 基 丙 異 0 基 甲 氟三 經濟部中央標準局員工消費合作社印製1,1-dimethyl-2- [N- (2-methoxymethoxy-4-trifluoromethylphenyl) benzenesulfonylamino] ethanol (380 mg; synthesized from Reference Example 22) in THF ( 4.0ml) solution, 6N osmic acid (0.8al) was added, and stirred at room temperature for 2 days. The reaction mixture was diluted with ethyl acetate, washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1) to obtain the title compound (291 mg) having the following physical data. ). TLC: Rf 0 · 29 (Benzene: Propylamidine = 9: 1) Refer to Example 24 — (Please read the precautions on the back before filling in this page.) Printed by the Consumer Standards Cooperative of the Ministry of Standards

3C3C

例 考 參 由 /ί\ 醚 基 甲 氧 甲 基 苯 基 甲 氟三 I 5 - 基 胺 - 2 用 使 得 作 操 同 相 之 3 2 例 考 參 -&gt; 7 11 例 施 實 -&gt; 2 例 考 參 依 \«/ 成 合 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 181 3 9 33 1 經濟部中央標準局員工消費合作社印製 523506 Α7 Β7 五、發明説明（182) 具下列物理數據之標題化合物。 TLC: Rf 0.57(己烷•·乙酸乙 _=5:2) 奮）fe例23 4-[2-[N-(2-羥基-2-甲基丙基）-苯磺醢胺基]-5-三氟甲基 苯氧甲基]苯甲酸Case study reference / 3 \ Ethyl methoxymethyl phenyl methyl fluorotri I 5-based amine-2 used to make the same phase of 3 2 cases reference-> 7 11 cases of implementation-> 2 cases Participation \ «/ Chenghe paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297mm) 181 3 9 33 1 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 523506 Α7 Β7 V. Description of the invention (182) The title compound of the following physical data. TLC: Rf 0.57 (Hexane ·· Ethyl acetate_ = 5: 2) Fen) Example 23 4- [2- [N- (2-hydroxy-2-methylpropyl) -benzenesulfonylamino]- 5-trifluoromethylphenoxymethyl] benzoic acid

使用1,1-二甲基-2-[H-(2-羥基-4-三氟甲基苯基）-苯 磺醯胺基]乙醇（由參考例23合成），依參考例64實施例2 之相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.48(氯仿：甲酵·•乙酸=100: 5:1) NHR(CD3COCD3) ： δ 8·03(2Η,brd,J = 8·2Hz) , 7.47-7,66( 4H,m)，7·30-7·47(6Η，ιη)，5·21(1Η,ιη), 4·89(1Η,πι), 3·79(2Η,s) , 1·20 (6Η，s) 管 _ 例 2 3 ( 1 ) - 2 3 ( 使用2 - [ Ν - ( 2 -羥基-2 -甲基丙基）-苯碌醸胺基卜5 -三 氟甲基鼢（由參考例23合成），依參考例64實施例2之相同 操作，得具下列物理數據之標題化合物。 審_例2 3 (Ί ) 4-[2-[Ν-(2-經基-2-甲基丙基）-苯碌醢胺基]-5-三氟甲基 ——-------會II (請先閲讀背面之注意事項再填寫本頁) 訂 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） 182 393 3 1 523506 A7 B7 五、發明説明（183) 苯氧甲基]桂皮酸Using 1,1-dimethyl-2- [H- (2-hydroxy-4-trifluoromethylphenyl) -benzenesulfonamido] ethanol (synthesized from Reference Example 23), according to Reference Example 64, Example The same operation as 2 can obtain the title compound with the following physical data. TLC: Rf 0.48 (chloroform: formazan · acetic acid = 100: 5: 1) NHR (CD3COCD3): δ 8 · 03 (2Η, brd, J = 8.2Hz), 7.47-7,66 (4H, m) , 7.30-7.47 (6 (, ιη), 5.21 (1Η, ιη), 4.89 (1Η, π), 3.79 (2Η, s), 1.20 (6Η, s) tube _ Example 2 3 (1)-2 3 (Using 2-[Ν-(2 -Hydroxy-2 -methylpropyl) -benzylamidob 5 -trifluoromethylphosphonium (synthesized from Reference Example 23) According to the same operation as in Example 2 of Reference Example 64, the title compound having the following physical data was obtained. Example 2 3 (Ί) 4- [2- [N- (2-Cryl-2-methylpropyl) -Benzamidine amine] -5-trifluoromethyl ——--------- Meeting II (Please read the notes on the back before filling this page) The size of the paper is applicable to the Chinese National Standard (CNS) Α4 Specifications (210 × 297 mm) 182 393 3 1 523506 A7 B7 V. Description of the invention (183) Phenoxymethyl] cinnamic acid

COOH T L C : R f 0.53 (氛仿·•甲酵=9 ·· 1) ·， 7 (6Η, m), 6.49 (1H, d, NMR ： δ 7.80 (1H, d, J=16.0Hz), 7.54 (6H, m), 7.3b 1 J=16.0Hz)，4.99 (1H，m), 4.81 (1H, m)，3.63 (2H, m), 1.21 (6H, s)〇 奮 例 2 3 ( 2 )4-[2-[H-(2-經基-2-甲基丙基卜笨磺釀胺基卜5_甲基苯氧 甲基]笨甲酸 --------_ — (請先閱讀背面之注意事項再填寫本頁) 訂 經濟部中央標準局員工消費合作社印製COOH TLC: R f 0.53 (Aromatic imitation · Formase = 9 ·· 1) ·, 7 (6Η, m), 6.49 (1H, d, NMR: δ 7.80 (1H, d, J = 16.0Hz), 7.54 (6H, m), 7.3b 1 J = 16.0Hz), 4.99 (1H, m), 4.81 (1H, m), 3.63 (2H, m), 1.21 (6H, s). Example 2 3 (2) 4- [2- [H- (2-Cycloyl-2-methylpropylbenzylsulfonylaminomethyl 5-methylphenoxymethyl] benzyl formic acid --------_ — (please (Please read the notes on the back before filling out this page.) Ordered by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

COOH T L C : R f 〇.45 (氯仿：甲酵=9 ·· 1 ); NM R ： δ 8.09 (2Η, d, J=8.4Hz)f 7.60 (2H, m), 7.28-7.44 (5H, m), 7.06 (1 H, m), 6.71 (2H, m), 5.00 (1H, d, J-12.8Hz), 4.74 (1H, d, J=12.8Hz), 3.69 (1H, d, J=14.2Hz), 3.57 (1H, d, J=14.2Hz), 2.33 (3H, s), 2.13 (1H, s), 1.25 (3H, bs), 1.19 (3H, bs)〇 ( cnsTm^^ (21GX297公釐）183 3933 1 523506COOH TLC: R f 0.45 (chloroform: formazan = 9 ·· 1); NM R: δ 8.09 (2Η, d, J = 8.4Hz) f 7.60 (2H, m), 7.28-7.44 (5H, m ), 7.06 (1 H, m), 6.71 (2H, m), 5.00 (1H, d, J-12.8Hz), 4.74 (1H, d, J = 12.8Hz), 3.69 (1H, d, J = 14.2 Hz), 3.57 (1H, d, J = 14.2Hz), 2.33 (3H, s), 2.13 (1H, s), 1.25 (3H, bs), 1.19 (3H, bs) 〇 (cnsTm ^^ (21GX297) %) 183 3933 1 523506

A7 B7 五、發明説明（184) 啻_俐2 ：H 3 ) 4-[2-[N-(2-羥基-2-甲基丙基）-2-呋喃基磺醢胺基]-5 氟甲基苯氧甲基]苯甲酸A7 B7 V. Description of the invention (184) 啻 _ 莉 2: H 3) 4- [2- [N- (2-hydroxy-2-methylpropyl) -2-furylsulfonamido] -5 Fluorine Methylphenoxymethyl] benzoic acid

COOH NMR ： 5 8.15 (2H,d,J=8.4Hz), 7.52 (2H, d, J=8.4Hz), 7.21-7.34 (4H, m), 6.82 (1H，m), 6.38 (1H, m)，5·12 (2H, m), 3.76 (2H, m), 2·12 (1H, s)，1.23 (6H，bs)。 --------會II (請先閱讀背面之注意事項再填寫本頁) 訂 啻_例24 4-[2-(N-異丙基-笨磺醯胺基）-5-三氟甲基苯氧甲基]苯氧 乙酸COOH NMR: 5 8.15 (2H, d, J = 8.4Hz), 7.52 (2H, d, J = 8.4Hz), 7.21-7.34 (4H, m), 6.82 (1H, m), 6.38 (1H, m) , 5.12 (2H, m), 3.76 (2H, m), 2.12 (1H, s), 1.23 (6H, bs). -------- Meeting II (Please read the notes on the back before filling this page) Order_Example 24 4- [2- (N-isopropyl-benzylsulfonylamino) -5- 三Fluoromethylphenoxymethyl] phenoxyacetic acid

/C〇〇H 經滴部中央標準局員工消費合作社印製 F3/ C〇〇H Printed by the Consumers Cooperative of the Central Bureau of Standards of Didi F3

例 基考 丙參 異依 參得 由 ， ✓IV 作 操 同 相 酚 基 甲 氟三 5-例 )-施 基實 胺-&gt;。 醯b)物 磺8(合 Μ 1 b ¾列彳 題 標 之 據 (H),數 CS3 成理 用合物 使24列 例下 考具 之 2 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 184 393 3 1 523506 A7 B7 五、發明説明（1 85) TLC: Rf 0.39(乙酸乙酯：己烷：乙酸=9:10:1) NHR： 57*80(2H&gt;d&gt;J=7.5Hz), 7.49(lH,t,J=7^5Hz), 7.40-7.20(7H,m)， 6.95(2H,d,J=8.5Hz), 4.98(2H,s), 4.72(2H,s), 4.28(lH,qn,J=6.5Hz), l*06(3H,d,J=6.5Hz ),1 · 01 (3H，d,J = 6·5Hz) g m m 24(1)-24(10) 使用對應化合物依參考例18(b)4實施例2相同操作， 得具下列物理數據之標題化合物。 啻_例24 (1) 5-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯氧甲基]α吩 -2 -接酸 (請先閲讀背面之注意事項再填寫本頁)Example: Basic test: Cs, Cs, and Cs, get IV, and IV as the same phase. Phenylmethyl fluorotrifluoro. 5)) -Stilbestamine- &gt;.醯 b) Physical sulfonate 8 (combined with M 1 b ¾ column 彳 title evidence (H), the number of CS3 logical use compound is 24 in the case of the test case 2 paper size applicable to the Chinese National Standard (CNS) A4 specifications (210X 297 mm) 184 393 3 1 523506 A7 B7 V. Description of the invention (1 85) TLC: Rf 0.39 (ethyl acetate: hexane: acetic acid = 9: 10: 1) NHR: 57 * 80 (2H &gt; d &gt; J = 7.5Hz), 7.49 (lH, t, J = 7 ^ 5Hz), 7.40-7.20 (7H, m), 6.95 (2H, d, J = 8.5Hz), 4.98 (2H, s), 4.72 ( 2H, s), 4.28 (lH, qn, J = 6.5Hz), l * 06 (3H, d, J = 6.5Hz), 1 · 01 (3H, d, J = 6.5Hz) gmm 24 (1) -24 (10) The title compound having the following physical data was obtained in the same manner as in Reference Example 18 (b) 4, Example 2 using the corresponding compound. 啻 _Example 24 (1) 5- [2- (N-isopropyl- Benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] αphen-2 -acid (please read the precautions on the back before filling this page)

QQ

NMR ： δ 7.9-7.7 (3Η, m), 7.6-7.3 (3H, m), 7.3-7.2 (3H, m), 7.16 (1H, d, J=4.0Hz), 5.20 (2H, s), 4.5-4.3 (1H, m), 1.10 (3H, d, J=3.8Hz), 1.32 (3H, d, J=3.8Hz)〇 經濟部中央標準局員工消費合作社印製 管_例24 m 5-[2-(N -異丙基-苯磺酿胺基）-5 -三氟甲基苯氧甲基]呋喃 -2-羧酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 185 39 33 1 523506 A7 B7 五、發明説明（186) ηNMR: δ 7.9-7.7 (3Η, m), 7.6-7.3 (3H, m), 7.3-7.2 (3H, m), 7.16 (1H, d, J = 4.0Hz), 5.20 (2H, s), 4.5 -4.3 (1H, m), 1.10 (3H, d, J = 3.8Hz), 1.32 (3H, d, J = 3.8Hz) 〇 Printed tube by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs_Example 24 m 5- [ 2- (N -isopropyl-benzenesulfonylamino) -5 -trifluoromethylphenoxymethyl] furan-2-carboxylic acid The paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 185 39 33 1 523506 A7 B7 V. Description of the invention (186) η

C〇〇H NM R ： δ 7.76 (2H, d, J=8Hz), 7.54-7.29 (3H, m), 7.29-7.13 (4H, m), 6.52 (1 H, m), 5.00 (2H, s), 4.31 (1H, m), 0.98 (6H, m)〇 奮憲例2 4 ( 3 ) 4-[2-(H-異丙基-苯磺釀胺基）-5 -甲基苯氧甲基]苯氧乙酸C〇〇H NM R: δ 7.76 (2H, d, J = 8Hz), 7.54-7.29 (3H, m), 7.29-7.13 (4H, m), 6.52 (1 H, m), 5.00 (2H, s ), 4.31 (1H, m), 0.98 (6H, m). Example 2 4 (3) 4- [2- (H-isopropyl-benzenesulfonylamino) -5 -methylphenoxymethyl Phenyl] phenoxyacetic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

^C〇〇H T L C ： R f 0.09 (乙酸乙酯）； 經濟部中央標準局員工消費合作社印製 NMR ： δ 7.81 (2Η, d, J=7.5 Hz), 7.50-7.30 (5H, m), 7.00-6.91 (3H, m), 6.82-6.73 (2H ,m), 4.91 (2H, s), 4.71 (2H, s), 4.27 (1H, sept, J=7Hz), 2.36 (3H, s), 1.05 (3H, d, J=7Hz), 1.01 (3H，d, J=7Hz)。 管_例24 U) 、 5-[2-(N-異丙基-苯磺醯胺基）-5-甲基苯氧甲基]**吩_2_ 羧酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 186 3 933 1 523506 A7 B7 五、發明説明（187)^ C〇〇HTLC: R f 0.09 (ethyl acetate); NMR printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: δ 7.81 (2Η, d, J = 7.5 Hz), 7.50-7.30 (5H, m), 7.00 -6.91 (3H, m), 6.82-6.73 (2H, m), 4.91 (2H, s), 4.71 (2H, s), 4.27 (1H, sept, J = 7Hz), 2.36 (3H, s), 1.05 (3H, d, J = 7Hz), 1.01 (3H, d, J = 7Hz). Tube_Example 24 U), 5- [2- (N-isopropyl-benzenesulfonamido) -5-methylphenoxymethyl] ** phen_2_ carboxylic acid The paper size is applicable to Chinese national standards ( CNS) A4 specification (210X297 mm) 186 3 933 1 523506 A7 B7 V. Description of the invention (187)

COOH TLC ·· R f 0.30 (氯仿··甲酵=9 ·· 1); . NMR ： δ 7.9-7.7 (3H, m), 7.5-7.4 (1H, m), 7.4-7.3 (2H, m), 7.12 (1H, d, J=3.6Hz), 7.01 (1 H, d, J=8.2Hz), 6.9-6.7 (2H, m), 5.1 2 (2H, s), 4.5-4.3 (1 H, m), 2·38 (3H, s), 1 ·51 (3H，d，J=2.4Hz)，1.05 (3H, d, J=2.4Hz)。 奮淪例24 (5) 4-[2-(N-異丙基-笨磺釀胺基卜5*•甲基笨氧甲基]桂皮酸 (請先閲讀背面之注意事項再填寫本頁)COOH TLC ·· R f 0.30 (chloroform ·· formase = 9 ·· 1);. NMR: δ 7.9-7.7 (3H, m), 7.5-7.4 (1H, m), 7.4-7.3 (2H, m) , 7.12 (1H, d, J = 3.6Hz), 7.01 (1 H, d, J = 8.2Hz), 6.9-6.7 (2H, m), 5.1 2 (2H, s), 4.5-4.3 (1 H, m), 2.38 (3H, s), 1.51 (3H, d, J = 2.4Hz), 1.05 (3H, d, J = 2.4Hz). Example 24 (5) 4- [2- (N-Isopropyl-benzylsulfonamide 5 * • methylbenzyloxymethyl] cinnamic acid (Please read the precautions on the back before filling this page)

02S 經濟部中央標準局員工消費合作社印製 T L C ： R f 0.39 (己烷：乙酸乙酯=1:2); NM R ： δ 7.86-7.78 (3Η, m), 7.60-7.26 (7H, m), 6.97 (1 H, d, J=8Hz), 6.80-6.74 (2H, m), 6.48 (1 H, d, J=16Hz), 5.01 (2H, s), 4.36 (1 H, sept., J=6.5Hz), 1.05 (6H, d, J=6.5Hz)〇 奩餱例24 (6) 4-[2-(N-異丙基-苯磺醢胺基卜5-氯苯氧甲基]苯氧基乙酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 187 39 33 1 523506 A7 B7 五、發明説明（188)02S TLC printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs: R f 0.39 (hexane: ethyl acetate = 1: 2); NM R: δ 7.86-7.78 (3Η, m), 7.60-7.26 (7H, m) , 6.97 (1 H, d, J = 8Hz), 6.80-6.74 (2H, m), 6.48 (1 H, d, J = 16Hz), 5.01 (2H, s), 4.36 (1 H, sept., J = 6.5Hz), 1.05 (6H, d, J = 6.5Hz). Example 24 (6) 4- [2- (N-Isopropyl-benzenesulfonamido 5-chlorophenoxymethyl) Phenoxyacetic acid The paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 187 39 33 1 523506 A7 B7 V. Description of the invention (188)

/C〇〇H/ C〇〇H

T L C : R f〇·1〇（氯仿：甲醇=1 〇 : 1 ); NMR ： δ 7.80-7.76 (2Η, m), 7.52-7.44 (1H, m), 7.35-7.26 (4H, m), 7.05-6.91 (5H, m)，4.91 (2H，s), 4.72 (2H，s)，4.28 (1 H,七峯，J二7Hz), 1.05 (3H，d，J=7Hz)， 1.00 (2H, d, J=7Hz)〇 啻）fe俐24 m 4-[2-(h-異丙基-苯磺醢胺基卜5-氯苯氧甲基]桂皮酸TLC: R f〇 · 10 (chloroform: methanol = 1 〇: 1); NMR: δ 7.80-7.76 (2Η, m), 7.52-7.44 (1H, m), 7.35-7.26 (4H, m), 7.05 -6.91 (5H, m), 4.91 (2H, s), 4.72 (2H, s), 4.28 (1 H, seven peaks, J 2 7Hz), 1.05 (3H, d, J = 7Hz), 1.00 (2H, d, J = 7Hz) 〇 啻) fe 24 m 4- [2- (h-isopropyl-benzenesulfonamido 5-chlorophenoxymethyl] cinnamic acid

經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) τ L C ： R f 0.31 (己烷··乙酸乙酯=1:1); NM R ： δ 7.85-7.77 (2Η, m), 7.60^7.35 (7H, m), 7Ό5-6.90 (3H, m), 6.48 (1 H, d, J=16Hz)，5.01 (2H, s)，4.36 (1 H,七峯，J=6.5Hz), 1.04 (6H、，d, J=7Hz)。 n m m 2A (&amp;) 5-[2-(N-異丙基-苯磺釀胺基）-5-氯苯氧甲基]**吩-後 酸 本紙張尺度適用中國國家標準（CNS ) A4規格（2丨〇乂297公t ) 188 3933 1 523506 A7 B7 五、發明説明（189)Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) τ LC: R f 0.31 (hexane ·· ethyl acetate = 1: 1); NM R: δ 7.85-7.77 (2Η, m), 7.60 ^ 7.35 (7H, m), 7Ό5-6.90 (3H, m), 6.48 (1 H, d, J = 16Hz), 5.01 (2H, s), 4.36 (1 H, seven peaks , J = 6.5Hz), 1.04 (6H ,, d, J = 7Hz). nmm 2A (&amp;) 5- [2- (N-Isopropyl-benzenesulfonylamino) -5-chlorophenoxymethyl] ** phene-postacid This paper size applies to Chinese National Standard (CNS) A4 Specification (2 丨 〇297297 t) 188 3933 1 523506 A7 B7 V. Description of the invention (189)

COOHCOOH

T L C ： R f 0.42 (氯仿：甲醇= 9:1); NMR ： δ 7.8-7.7 (3Η, m), 7.5-7.3 (3H, m), 7.2-6.9 (4H, m), 5.15 (1H, d, J=13.2Hz), 5.08 (1H, d, J=13.2Hz), 4.5-4.3 (1H, m), 5.5-4.0 (1H, br), 1.08 (3H, d, J=2.6Hz)，1.05 (3H, d, J=2.6Hz)。 奮淪俐24 (9) 5-[2-(N-異丙基-苯磺醵胺基）-5-氯苯氧甲基]呋喃-2-羧 酸 (請先閱讀背面之注意事項再填寫本頁)TLC: R f 0.42 (chloroform: methanol = 9: 1); NMR: δ 7.8-7.7 (3Η, m), 7.5-7.3 (3H, m), 7.2-6.9 (4H, m), 5.15 (1H, d , J = 13.2Hz), 5.08 (1H, d, J = 13.2Hz), 4.5-4.3 (1H, m), 5.5-4.0 (1H, br), 1.08 (3H, d, J = 2.6Hz), 1.05 (3H, d, J = 2.6Hz). Fenrenli 24 (9) 5- [2- (N-Isopropyl-benzenesulfonamido) -5-chlorophenoxymethyl] furan-2-carboxylic acid (Please read the precautions on the back before filling (This page)

COOH T L C : R f 〇.37 (氛汸··甲酵=9 : 1 ); 經濟部中央標準局員工消費合作社印製 NM R ： δ 7.9-7.7 (2H, m), 7.6-7.4 (3H, m), 7.31 (1 H, d, J-3.4Hz)( 7.0*6.9 (3H, m), 6.63 (1 H, d, J=3.4Hz), 5.03 (1 H, d, J=1 3.2Hz), 4.96 (1 H, d, J = 1 3.2Hz), 5.5-4.5 (1 H, br), 4.4-4.2 (1 H, m), 1.03 (6H, d, J-6.6Hz)〇 奮 _ 例 2 4 (1 0 ) 4-[2-[2-(N-異丙基-苯磺釀胺基）-5-三氟甲基苯氧基]乙 基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 189 3933 1 523506COOH TLC: R f 〇.37 (aerobic ·· formase = 9: 1); NM R printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs: δ 7.9-7.7 (2H, m), 7.6-7.4 (3H, m), 7.31 (1 H, d, J-3.4Hz) (7.0 * 6.9 (3H, m), 6.63 (1 H, d, J = 3.4Hz), 5.03 (1 H, d, J = 1 3.2Hz ), 4.96 (1 H, d, J = 1 3.2Hz), 5.5-4.5 (1 H, br), 4.4-4.2 (1 H, m), 1.03 (6H, d, J-6.6Hz) Example 2 4 (1 0) 4- [2- [2- (N-isopropyl-benzenesulfonylamino) -5-trifluoromethylphenoxy] ethyl] benzoic acid Standard (CNS) A4 size (210X297 mm) 189 3933 1 523506

A7 — B7 五、發明説明（190) F3 C 0 \C 〇〇 Η o2s T L C : R f 0.40 (氯仿：甲醇= 9:1); NMR ： δ 8.07 (2H, d, J=8.5Hz), 7.83 (2H, d, J=7Hz),7.65-7.45 (5H, m), 7.39 (2H, d, J=8.5Hz), 7.25-7.08 (3H, m), 4.37 (1 H, m), 4.25-4.05 (2H, m), 3.08 (2H, d, J=7Hz), 0.99 (3H, d, J=6.5Hz), 0.84 (3H, d, J=6.5Hz)〇 管嫵例25 2-甲氧基- 4-[2-(N-異丙基-苯磺醮胺基）-5-三氟甲基苯氧 甲基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)A7 — B7 V. Description of the invention (190) F3 C 0 \ C 〇〇Η o2s TLC: R f 0.40 (chloroform: methanol = 9: 1); NMR: δ 8.07 (2H, d, J = 8.5Hz), 7.83 (2H, d, J = 7Hz), 7.65-7.45 (5H, m), 7.39 (2H, d, J = 8.5Hz), 7.25-7.08 (3H, m), 4.37 (1 H, m), 4.25- 4.05 (2H, m), 3.08 (2H, d, J = 7Hz), 0.99 (3H, d, J = 6.5Hz), 0.84 (3H, d, J = 6.5Hz). Example 25 2-methoxy -4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 使用2-(N-異丙基-苯磺醢胺基）-5-三氟甲基酚（由參 考例24合成），依參考例64實施例2般操作，得具下列物 理數據之標題化合物。 TLC:Rf 0.49(氯仿··甲醇=9:1) 、 NMR: S 11.0-10.6(lH,br), 8.21(lH，d,J=7.8Hz), 7·9-7*8(2H，m)，7*71(lH，d，J:0.6Hz), 7·7-7·4(3Η,πι)， 7·3_7·2(2Η,βι)，7·2-7·1(1Η，腿），7.〇〇(iH,d，J = 7.8Hz)， 5.22(2H,s), 4·6-4·4(1Η,πι), 4.18(3H,s), 1.08(3H，d, 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 190 39331 523506 kl B7 五、發明説明（191) J = 6 · 6Hz)，0 · 92 (3H,d,J = 6♦6Hz) g _ 例 26 (請先閲讀背面之注意事項再填寫本頁) 2-羥基- 4-[2-(N-異丙基-笨磺酿胺基）-5-三氟甲基苯氧甲 基]苯甲酸Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, using 2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenol (synthesized from Reference Example 24). By operation, the title compound having the following physical data was obtained. TLC: Rf 0.49 (chloroform · methanol = 9: 1), NMR: S 11.0-10.6 (lH, br), 8.21 (lH, d, J = 7.8Hz), 7.9-9 * 8 (2H, m ), 7 * 71 (lH, d, J: 0.6Hz), 7 · 7-7 · 4 (3Η, π), 7 · 3_7.2 · 2 (2Η, β), 7 · 2-7 · 1 (1Η, Leg), 7.〇〇 (iH, d, J = 7.8Hz), 5.22 (2H, s), 4.6-4 · 4 (1Η, πm), 4.18 (3H, s), 1.08 (3H, d , This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) 190 39331 523506 kl B7 V. Description of the invention (191) J = 6 · 6Hz), 0 · 92 (3H, d, J = 6 ♦ 6Hz ) g _ Example 26 (Please read the precautions on the back before filling this page) 2-Hydroxy-4- [2- (N-isopropyl-benzylsulfonylamino) -5-trifluoromethylphenoxymethyl Phenyl] benzoic acid

使用2-(N-異丙基-苯磺醢胺基）-5-三氟甲基酚（由參 考例24合成），依參考例64參考例234實施例2之相同操 作，得具下列物理數據之標題化合物。 TLC: Rf 0,56(氯仿··甲醇：乙酸=90:9:1); HMR： δ 10-51(lH,s), 7·95(1 Η ,d,J = 8·0 Ηz) , 7.9-7-8( 2H,m), 7·6-7·4(3Η,πι), 7·3-7·2(3Η,πι), 7·1-7·0(2Η,βι) ,5.05(2H,s), 4·5-4·3(1Η,ιβ), 1.09(3H,d,J = 5.0Hz), 1·06 (3Η,d , J = 5 · ΟΗζ) 經濟部中央標準局員工消費合作社印製 例 施 奮 例 考 參 物 含 化 &gt; 題 6 標 例之 考據 參數 依理 , 物 物列 合下 化具 應得 對 ， 用作 使操 同 相 之 2 例 施 實 基 羥 酸 甲 苯 基 胺 醯 磺 苯 - 基 丙 異 基 甲 氧 苯 基 甲 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） 191 39 33 1 523506 A7 B7 32 (3H，m)， 2.35 (3H，s)’ 五、發明説明U 92)Using 2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenol (synthesized from Reference Example 24), following the same operation as Reference Example 64, Reference Example 234, and Example 2, the following physical properties were obtained: Data title compound. TLC: Rf 0,56 (chloroform · methanol: acetic acid = 90: 9: 1); HMR: δ 10-51 (lH, s), 7.95 (1 Η, d, J = 8.0 Ηz), 7.9-7-8 (2H, m), July · 6-7 · 4 (3Η, πι), July · 3-7 · 2 (3Η, πι), July · 1-7 · 0 (2Η, βι), 5.05 (2H, s), 4.5-5-4 · 3 (1Η, ιβ), 1.09 (3H, d, J = 5.0Hz), 1.06 (3Η, d, J = 5 · Ο ζ) Central Standards of the Ministry of Economic Affairs Bureau Consumer Consumption Cooperatives Printed Examples Shi Fenxian Reference Material Containment> Question 6 The criteria of the standard examples are based on the rationale, the combination of the materials should be correct, used to make the same phase in 2 cases Amine sulfonyl- propyl isopropyl methoxyphenylmethyl This paper is sized for the Chinese National Standard (CNS) A4 (210 × 297 mm) 191 39 33 1 523506 A7 B7 32 (3H, m), 2.35 (3H, s) 'V. Description of Invention U 92)

TLC : R f 〇.20 (氯仿：甲酵=17:3); NMR : δ 10.50 (1H，s), 7.92 (1H，d, J=8.5Hz)，7.83 (2H，m)，7.54 7.05-6.93 (3H, m)，6.81-6.72 (2H，m)，4·97 (2H，s)，4.42 (1H，πι)， 1.13-0.98 (6H, m)〇 n m m (2) 2-羥基-4-[2-(N-異丙基-苯磺釀胺基）-5-氯苯氧甲基]苯 甲酸 I · m · = - (H -- ........... ..... - «I C請先閱讀背面之注意事項存填寫本買)TLC: R f 0.20 (chloroform: formazan = 17: 3); NMR: δ 10.50 (1H, s), 7.92 (1H, d, J = 8.5Hz), 7.83 (2H, m), 7.54 7.05- 6.93 (3H, m), 6.81-6.72 (2H, m), 4.97 (2H, s), 4.42 (1H, m), 1.13-0.98 (6H, m), onm (2) 2-hydroxy-4 -[2- (N-Isopropyl-benzenesulfonylamino) -5-chlorophenoxymethyl] benzoic acid I · m · =-(H-............ ....-«IC Please read the precautions on the back and fill in this purchase)

經濟部中央標準局員工消費合作社印製 τ L C ： R f 0.21 (氛仿：甲醇=9 : 1 ); NMR ； 5 7.93 (1H, d, J=8.0Hz), 7.9-77 (2H, m), 7.6-7.3 (3H, m), 7.1-6.9 (5H, m), 4.97 (2H, s), 4.5-4.3 (1 H, m), 3Ό-2.0 (2H, br), 1.07 (3H, d, J=6.2Hz), 1.04 (3H, d, J=6.2Hz)〇 乂 參者例2 5 4 -苯磺醢胺基-3 -硝基苄基三氟化物 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 192 523506 A7 B7 五、發明説明（193)Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs τ LC: R f 0.21 (Fluent: methanol = 9: 1); NMR; 5 7.93 (1H, d, J = 8.0Hz), 7.9-77 (2H, m) , 7.6-7.3 (3H, m), 7.1-6.9 (5H, m), 4.97 (2H, s), 4.5-4.3 (1 H, m), 3Ό-2.0 (2H, br), 1.07 (3H, d , J = 6.2 Hz), 1.04 (3H, d, J = 6.2 Hz). Example of reference 2 5 4 -benzenesulfonamido-3 -nitrobenzyl trifluoride This paper applies Chinese national standards ( CNS) A4 specification (210X297 mm) 192 523506 A7 B7 V. Description of the invention (193)

4-胺基-3-硝基苄基三氟化物（3.09克）之THF溶液中， 添加氫化鈉（ 660mg),室溫下搅拌30分鐘後，添加苯磺醯 氯（3.18g),室溫下攪拌2小時，再添加氫化納（420mg), 攪拌1小時。反應混合物中添加氯化銨溶液使呈酸性，K 乙酸乙酯萃取。有機層予K洗淨、乾燥、過濾並濃縮，得 具下列物理數據之標題化合物（4.86g)。 TLC: Rf 0.31(己烷：乙酸乙酿=3:1)。 參者例26 4 -苯磺醯胺基-3-胺基苄基三氟化物 Ρ3〇^γΝΗ2To a solution of 4-amino-3-nitrobenzyl trifluoride (3.09 g) in THF was added sodium hydride (660 mg), and after stirring at room temperature for 30 minutes, benzenesulfonyl chloride (3.18 g) was added at room temperature. After stirring for 2 hours, sodium hydride (420 mg) was added thereto, followed by stirring for 1 hour. The reaction mixture was acidified by adding ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with K, dried, filtered and concentrated to obtain the title compound (4.86 g) having the following physical data. TLC: Rf 0.31 (hexane: ethyl acetate = 3: 1). Reference Example 26 4 -benzenesulfonamido-3-aminobenzyl trifluoride P3〇 ^ γΝΗ2

II

經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 使用4-苯磺醢胺基-3-硝基苄基三氟化物（2.4g;由參 考例25合成），依參考例12般相同操作/得具下列物理數 據之標題化合物（1.7g)。 TLC: Rf 0.17(己烷：乙酸乙酯=3:1)。 奮_例27 4-(2-苯磺醯胺基-5-三氟甲基苯基胺甲基）苯甲酸甲酯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 193 3 933 1 523506 A7 B7 五、發明説明（194)Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Use 4-benzenesulfonamido-3-nitrobenzyl trifluoride (2.4g; synthesized from Reference Example 25 ), The same operation as in Reference Example 12 was performed to obtain the title compound (1.7 g) having the following physical data. TLC: Rf 0.17 (hexane: ethyl acetate = 3: 1). Fen_Example 27 Methyl 4- (2-benzenesulfonamido-5-trifluoromethylphenylaminemethyl) benzoate This paper is sized to the Chinese National Standard (CNS) A4 (210X 297 mm) 193 3 933 1 523506 A7 B7 V. Description of the invention (194)

COOMe (請先閱讀背面之注意事項再填寫本頁) 4-苯磺酿胺基-3-胺基苄基三氟化物（lOOiag;由參考例 26合成）及對甲醛基笨甲酸甲酯（78ing)之甲醇（2ml)溶液中 ，添加乙酸（1.5ml),室溫下搅拌2小時後，添加含氰硼氫 化納（30iag)之甲醇（2ml)溶液，室溫下搅拌2小時。反應液 Μ水-乙酸乙酯萃取，洗淨、乾燥、過濾、濃縮，析出之 結晶Μ己烷洗淨，得具下列物理數據之標題化合物（146 mg TLC: Rf 0.27(己烷：乙酸乙酯=2:1); NHR： S8.02(2H,m), 7.76(2H,m), 7·6-7.4(5Η,πι), 6·74 _6.70(2H,m)，6·55-6·50(1Η,βι), 6.02(lH,bs), 5.35(1Η ,m) , 4 · 40 (2Η , in) , 3 · 92 (3Η , s) 實施u倒. . ..2A. 經滴部中央標準局員工消費合作社印製 4-[2-(N-異丙基-苯磺釀胺基）-5-三氟甲基苯基胺甲基]苯 甲酸COOMe (Please read the precautions on the back before filling this page) 4-benzenesulfonylamino-3-aminobenzyl trifluoride (100iag; synthesized from Reference Example 26) and p-formyl methyl benzoate (78ing ) In a methanol (2 ml) solution, acetic acid (1.5 ml) was added, and the mixture was stirred at room temperature for 2 hours. Then, a solution of sodium cyanoborohydride (30iag) in methanol (2 ml) was added, and the mixture was stirred at room temperature for 2 hours. The reaction solution was extracted with water and ethyl acetate, washed, dried, filtered, and concentrated. The precipitated crystals were washed with hexane to obtain the title compound (146 mg TLC: Rf 0.27 (hexane: ethyl acetate) = 2: 1); NHR: S8.02 (2H, m), 7.76 (2H, m), 7.6-7.4 (5Η, πι), 6.74 _6.70 (2H, m), 6.55 -6 · 50 (1Η, βι), 6.02 (lH, bs), 5.35 (1Η, m), 4.40 (2Η, in), 3.92 (3Η, s) Implementation of u ... Printed by 4- [2- (N-isopropyl-benzenesulfonylamino) -5-trifluoromethylphenylaminemethyl] benzoic acid, printed by the Consumer Cooperatives of the Central Standards Bureau of Didi

C〇〇H 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 194 3933 1 523506 A7 B7 五、發明説明（195) 使用4-(2-苯磺醢胺基-5-三氟甲基苯基胺甲基）苯甲 酸甲酯（由實施例27合成），依實施例174實施例2之相同 操作，得具下列物理數據之標題化合物。 TLC: Rf 0.45(己烷：乙酸乙酷=1:1); NHR： 5 8.10(2H,d,J = 8.5Hz), 7·8-7.7(2Η,βι), 7.6-7.4( 5H,m), 6·8-6·7(2Η，π〇, 6.7-6.6(lH,m), 5.34(lH,m), 4.69(lH,sept,J=7Hz), 4*45(2H,d,J=6Hz), 1.15(3H,d, J = 7Hz)，1 · 01 (3H , d , J = 7Hz) 奮_例29 4-[N-甲基-[2-(N-異丙基-苯磺醸胺基）-5-三氟甲基苯基] 胺甲基]苯甲酸甲酯 ^\.COOMe (請先閱讀背面之注意事項再填寫本頁)C〇〇H This paper size is applicable to Chinese National Standard (CNS) A4 specification (210X 297 mm) 194 3933 1 523506 A7 B7 V. Description of the invention (195) Use 4- (2-benzenesulfonamido-5-three Fluoromethylphenylaminemethyl) methyl benzoate (synthesized from Example 27) was carried out in the same manner as in Example 174 and Example 2 to obtain the title compound with the following physical data. TLC: Rf 0.45 (hexane: ethyl acetate = 1: 1); NHR: 5 8.10 (2H, d, J = 8.5Hz), 7.8-7.7 (2Η, βι), 7.6-7.4 (5H, m ), 6 · 8-6 · 7 (2Η, π〇, 6.7-6.6 (lH, m), 5.34 (lH, m), 4.69 (lH, sept, J = 7Hz), 4 * 45 (2H, d, J = 6Hz), 1.15 (3H, d, J = 7Hz), 1 · 01 (3H, d, J = 7Hz) Fen_Example 29 4- [N-methyl- [2- (N-isopropyl- Benzenesulfonylamino) -5-trifluoromethylphenyl] aminemethyl] methyl benzoate ^ \. COOMe (Please read the precautions on the back before filling in this page)

經濟部中央標準局員工消費合作社印製 使用4-(2-苯磺釀胺基-5-三氟甲基苯基胺甲基）苯甲 酸甲酯（由實施例27合成），依實施例17般操作，所得之4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯基胺甲基]苯甲 酸甲酯（200mg)溶於DMF(5ml)中，添加氫化納（64mg)及碘 甲烷（200// 1),在601搅拌24小時。反應混合物Μ水-乙 酸乙酯萃取、洗淨、乾燥、過滤及減壓濃縮。殘留物以矽 膠管柱層析法（己烷：乙酸乙酯=5:1)純化，得具下列物理 數據之標題化合物（105ing)。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 195 39 33 1 523506 A7 B7 五、發明説明（196) TLC: Rf 0.54(二氯甲烷）； NMR: S8.0(2H,ni), 7.9(2H,m), 7·6-7·5(3Η,πι), 7·4( 2H,m), 7·4-7·2(2Η,ιβ), 7·0(1Η,βι), 4·6·4·3(2Η,πι), 3·92(3Η,ιβ), 2.72(3H,s), 1·2(3Η,ιβ), 0·8(3Η,ιβ) 管）fe例30 4-[Ν-甲基-[2-(Ν-異丙基-苯磺釀胺基）-5-三氟甲基苯基] 胺甲基]苯甲酸Printed using 4- (2-benzenesulfonylamino-5-trifluoromethylphenylaminemethyl) benzoic acid methyl ester (synthesized from Example 27) by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs, according to Example 17 The general operation, the obtained 4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenylamine methyl] benzoate methyl ester (200mg) was dissolved in DMF (5ml) Then, add sodium hydride (64 mg) and methyl iodide (200 // 1), and stir at 601 for 24 hours. The reaction mixture was extracted with water-ethyl acetate, washed, dried, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to give the title compound (105ing) with the following physical data. This paper size is in accordance with Chinese National Standard (CNS) A4 (210X 297 mm) 195 39 33 1 523506 A7 B7 V. Description of the invention (196) TLC: Rf 0.54 (dichloromethane); NMR: S8.0 (2H, ni), 7.9 (2H, m), July 6-7 · 5 (3Η, π), July 4 (2H, m), July 4-7 · 2 (2Η, ιβ), 7.0 (1Η , βι), 4 · 6 · 4 · 3 (2Η, πι), 3.92 (3Η, ιβ), 2.72 (3H, s), 1.2 (3ι, ιβ), 0 · 8 (3Η, ιβ) Tube) fe Example 30 4- [N-methyl- [2- (N-isopropyl-benzenesulfonylamino) -5-trifluoromethylphenyl] aminemethyl] benzoic acid

使用4-[Ν-甲基-[2-(Ν-異丙基-苯磺釀胺基）-5-三氟 甲基苯基]胺甲基]苯甲酸甲酯（由實施例29合成），依實施 例2之相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.45(己烷：乙酸乙酯=1:1); NHR： 5 8,09(2H,d,J = 8Hz), 7.9(2H,ia), 7.7-7.4(5H,m), 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 7·2(2Η，ιη), 7·0(1Η,ιη)，4·6-4·4(3Η,πι), 2.75(3H,s), 1.26(3H,d,J=7Hz), 0*85(3H,d,J=7Hz) 參者例27 、 2-第三丁氧羰胺基-5-三氟甲基苯甲酸甲酿 Ο Ο M eUsing methyl 4- [N-methyl- [2- (N-isopropyl-benzenesulfonylamino) -5-trifluoromethylphenyl] aminemethyl] benzoate (synthesized from Example 29) Following the same procedure as in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.45 (hexane: ethyl acetate = 1: 1); NHR: 5 8,09 (2H, d, J = 8Hz), 7.9 (2H, ia), 7.7-7.4 (5H, m), economic Printed by the Consumer Standards Cooperative of the Ministry of Standards of the People's Republic of China (Please read the notes on the back before filling this page) 7 · 2 (2Η, ιη), 7.0 · (1Η, ιη), 4 · 6-4 · 4 (3Η, π), 2.75 (3H, s), 1.26 (3H, d, J = 7Hz), 0 * 85 (3H, d, J = 7Hz) See Example 27, 2-Third-butoxycarbonylamino-5- Trifluoromethylbenzoic acid methyl alcohol 〇 Ο M e

XI NHCOO—~—- 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 196 3 9 3 3 1 523506 A7 B7 五、發明説明（197) 4-第三丁氧羰胺基苄基三氟化物（3.90g)溶於THF中， 在-501下滴加第三丁基鋰（30rol),在- 501C搅拌3小時。 在攪拌下於其中加入碳酸氣體（溫度上升至- 30ρ左右）， 蒸除溶劑，M2H氫氧化納-乙醚混合溶液逆萃取。水層Μ 2Ν塩酸酸化，以乙醚萃取，洗淨並乾燥。逆萃取之乙醚層 予Μ洗淨、乾燥、過濾，與先前之乙醚層混合並濃縮，得 粗生成物。所得粗生成物Μ乙醚溶解，添加重氮甲烷之乙 醚溶液至反應液中直至呈黃色。反應液予以濃縮，Κ矽膠 管柱層析法（己烷：乙酸乙酯= 20:1410:1)純化，得具下列 物理數據之標題化合物（3.80g)。 TLC: Rf 0.70(己烷：乙酸乙酯=3:1)。 參考例2 8 2-胺基-5-三氟甲基苯甲酸甲酯 F3C^^/〇〇〇Me ^^nh2 2 -第三丁氧羰胺基-5-三氟甲基笨甲酸甲酯（3.80g; 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 由參考例27合成）之二氯甲烷（30ml)溶液中，添加三氟乙 酸（6ml),室溫下攪拌8小時。蒸除溶劑，Μ甲笨共沸3次 。反應物中添加水-碳酸氫鈉溶液使呈中性，以乙酸乙酯 萃取、洗淨、乾燥、過滤及濃縮。殘留物Μ矽膠管柱層析 法（己烷：乙酸乙酯= 5:1)純化，得具下列物理數據之標題 化合物（2 · 3 5 g )。 TLC: Rf 0.20(己烷：乙酸乙酯=5:1)。 h 奮施例31 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 197 3 9 3 3 1 523506 Α7 Β7 經濟部中央標準局員工消費合作社印製 五、發明説明（1 98) 4-[2-(N-異丙基-苯磺醢胺基）-5-三氟甲基苯甲醢胺基]苯 甲酸XI NHCOO— ~ —- This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X297 mm) 196 3 9 3 3 1 523506 A7 B7 V. Description of the invention (197) 4-third butoxycarbonylamino benzyl Trifluoride (3.90 g) was dissolved in THF, and tertiary butyl lithium (30rol) was added dropwise at -501, followed by stirring at -501C for 3 hours. Under stirring, carbonic acid gas was added thereto (the temperature rose to about -30ρ), the solvent was distilled off, and the M2H sodium hydroxide-ether mixed solution was back-extracted. The aqueous layer was acidified with M 2N, extracted with ether, washed and dried. The ether layer extracted back was washed, dried, filtered, mixed with the previous ether layer, and concentrated to obtain a crude product. The obtained crude product M was dissolved in diethyl ether, and an ethyl ether solution of diazomethane was added to the reaction solution until yellow. The reaction solution was concentrated and purified by K silica gel column chromatography (hexane: ethyl acetate = 20: 1410: 1) to obtain the title compound (3.80 g) having the following physical data. TLC: Rf 0.70 (hexane: ethyl acetate = 3: 1). Reference Example 2 8 2-Amino-5-trifluoromethylbenzoic acid methyl ester F3C ^^ / 〇〇〇〇Me ^ nh2 2 -Third-butoxycarbonylamino-5-trifluoromethylbenzylic acid methyl ester (3.80g; printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) synthesized from Reference Example 27) in dichloromethane (30ml) solution, add trifluoroacetic acid (6ml) Stir at room temperature for 8 hours. The solvent was distilled off, and the methyl formaldehyde was azeotroped 3 times. The reaction was neutralized by adding a water-sodium bicarbonate solution, and extracted with ethyl acetate, washed, dried, filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 5: 1) to obtain the title compound (2.35 g) having the following physical data. TLC: Rf 0.20 (hexane: ethyl acetate = 5: 1). h Fenshi 31 This paper size applies the Chinese National Standard (CNS) A4 specification (210X297 mm) 197 3 9 3 3 1 523506 Α7 Β7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (1 98) 4 -[2- (N-Isopropyl-benzenesulfonamido) -5-trifluoromethylbenzylamido] benzoic acid

02S02S

COOH 使用2-胺基-5-三氟甲基苯甲酸甲酯（由參考例28合成 ),依參考例24參考例34實施例14實施例2之相同操作 ,得具下列物理數據之標題化合物。 TLC: Rf 0.25(己烷：乙酸乙酯=1:2); NMR： S10.01(lH,s), 8·18-8·14(3Η,πι), 7.93((8H,a), 6.64(lH,d,J = 8Hz), 4·67(1Η,七峯，J = 6.5Hz), 1·09(3Η, d,J=6-5Hz), 0.86(3H,d,J=6.5Hz) 參者例29 4-[2-[N-[l,3-雙（第三丁基二甲基矽氧基）丙-2-基]-苯碌 醯胺基]-5-三氟甲基苯氧甲基]笨甲酸甲酯 (a) 1,3-OTBs體（中間體） OH TBs〇、丄 OTBsCOOH uses methyl 2-amino-5-trifluoromethylbenzoate (synthesized from Reference Example 28), following the same operation as Reference Example 24, Reference Example 34, Example 14, Example 2 to obtain the title compound with the following physical data . TLC: Rf 0.25 (hexane: ethyl acetate = 1: 2); NMR: S10.01 (lH, s), 8.18-8 · 14 (3Η, πm), 7.93 ((8H, a), 6.64 (lH, d, J = 8Hz), 4.67 (1Η, Seven Peaks, J = 6.5Hz), 1.09 (3Η, d, J = 6-5Hz), 0.86 (3H, d, J = 6.5Hz ) Participant Example 29 4- [2- [N- [l, 3-bis (third butyldimethylsiloxy) prop-2-yl] -benzylamine] -5-trifluoromethyl Phenoxymethyl] methyl benzoate (a) 1,3-OTBs body (intermediate) OH TBs〇, 丄 OTBs

含丙三醇（2g)之DMF(15ml)溶液中，在Ο”下滴加含第 三丁基二甲基矽烷基氯（6.5g)及眯唑（3.3g)之DMF(8ml)溶 液，室溫下攪拌3小時。反應混合物中注入水，Μ乙酸乙 酯-己烷混合液（乙酸乙酯：己烷=1:1)萃取，洙淨、乾燥， 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ29?公釐） 198 3 9 3 3 1 ------------—— (請先閲讀背面之注意事項再填寫本頁) 、1Τ · 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（199) K矽膠管柱層析法純化，得具下列物理數據之1,3-二OTBs 體（5.8g)〇 TLC: Rf 0·5(己烷··乙酸乙酯=9:1)。 (b)目的物In a solution of glycerol (2 g) in DMF (15 ml), a solution of DMF (8 ml) containing third butyldimethylsilyl chloride (6.5 g) and oxazole (3.3 g) was added dropwise at Stir at room temperature for 3 hours. Water is poured into the reaction mixture, and the mixture is extracted with ethyl acetate-hexane mixture (ethyl acetate: hexane = 1: 1), cleaned and dried. This paper is in accordance with Chinese national standards (CNS ) Α4 specification (210 × 29? Mm) 198 3 9 3 3 1 ---------------- (Please read the precautions on the back before filling this page), 1T · 523506 A7 B7 Ministry of Economic Affairs Printed by the Consumer Standards Cooperative of the Central Bureau of Standards 5. Description of the invention (199) K silica gel column chromatography purification, 1,3-di OTBs (5.8g) with the following physical data was obtained. TLC: Rf 0 · 5 ( Alkane ·· ethyl acetate = 9: 1) (b) target substance

使用4-(2-苯磺醢胺基-5-三氟甲基笨氧甲基）苯甲酸 甲酯（180mg;由實施例15合成）及上述（a)所得之1,3 -diOTBS體（ 247ing),依實施例19之相同操作，得具下列物 理數據之標題化合物（200iag)。 TLC: Rf 0.28(己烷：乙酸乙酯=9:1)。 啻_例32 4-[2-[Ν-(1,3-二羥基丙-2-基）-苯磺醯胺基]-5-三氟甲基 苯氧甲基]苯甲酸甲酿Using methyl 4- (2-benzenesulfonamido-5-trifluoromethylbenzyloxymethyl) benzoate (180 mg; synthesized from Example 15) and the 1,3-diOTBS body obtained in (a) above ( 247ing), following the same procedure as in Example 19, the title compound (200iag) having the following physical data was obtained. TLC: Rf 0.28 (hexane: ethyl acetate = 9: 1).例 _Example 32 4- [2- [N- (1,3-dihydroxyprop-2-yl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzoic acid

n 〇 一Ο Η 4-[2-[Ν-[1,3-雙（第三丁基二甲基矽氧基）丙-2-基]-苯磺醯胺基]-5-三氟甲基苯氧甲基]苯甲酸甲酯（200iag; 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 199 39 3 3 1 --------衣-- (請先閱讀背面之注意事項再填寫本頁) 訂 523506 Α7 Β7 五、發明説明（2 00) 由參考例29合成）之THF(3ml)溶液中，添加含氟化四丁銨 (0.57ml)之THF(IM)溶液，室溫下攪拌3小時。反應物中注 入水，Μ乙酸乙酯萃取，洗淨、乾燥，Μ矽膠管柱層析法 純化，得具下列物理數據之標題化合物（llOmg)。 TLC: Rf 0.50(二氯甲烷：甲醇=9:1)。 HMR: S8.08(2H,d，J=8.2Hz), 7,78(2H,d，J=7,2Hz), 7.70-7.24(8H,m), 5.14(lH,d,J=12.0Hz), 5.06(lH,d,J= 12·0Ηζ), 4·5 0- 4·30(1Η,ιη)，3.93(3H,s), 3.80-3.20( 4H，b), 2.72(lH,dd,J=3.6,18.2Hz) 管）fe例33 4-[2-[N-(l,3-二羥基丙-2-基）-苯磺釀胺基]-5-三氟甲基 苯氧甲基]笨甲酸n 〇 一 〇 Η 4- [2- [N- [1,3-bis (third butyldimethylsiloxy) prop-2-yl] -benzenesulfonylamino] -5-trifluoromethyl Methylphenoxymethyl] benzoate (200iag; this paper size applies to Chinese National Standard (CNS) A4 size (210X297 mm) 199 39 3 3 1 -------- clothing-(Please read first Note on the back, please fill in this page again.) Order 523506 Α7 Β7 V. Explanation of the invention (2 00) Synthesized from Reference Example 29) In THF (3ml) solution, add THF (IM) containing tetrabutylammonium fluoride (0.57ml) ) The solution was stirred at room temperature for 3 hours. The reaction product was poured into water, extracted with ethyl acetate, washed, dried, and purified by silica gel column chromatography to obtain the title compound (110 mg) having the following physical data. TLC: Rf 0.50 (dichloromethane: methanol = 9: 1). HMR: S8.08 (2H, d, J = 8.2Hz), 7,78 (2H, d, J = 7,2Hz), 7.70-7.24 (8H, m), 5.14 (lH, d, J = 12.0Hz ), 5.06 (lH, d, J = 12 · 0Ηζ), 4.5 · 0- 4.30 (1Η, ιη), 3.93 (3H, s), 3.80-3.20 (4H, b), 2.72 (lH, dd , J = 3.6, 18.2 Hz) tube) fe Example 33 4- [2- [N- (l, 3-dihydroxyprop-2-yl) -benzenesulfonylamino] -5-trifluoromethylphenoxy Methyl] stearic acid

經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 使用4-[2-[Ν-(1,3-二羥基丙-2-基）-苯磺醯胺基]-5 -三氟甲基苯氧甲基]苯甲酸甲酿（由實施例32合成），依實 施例2相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.51(乙酸乙酯：乙酸=99:1); NMR: S8.13(2H,d,J=8.4Hz), 7.8-7.7(2H,m), 7·6-7·2( 8H,m), 5.17(lH,d,J=11.4Hz), 5.08(lH,d,J=11.4Hz), 4·5-4·3(1Η,ιη), 3·6-3·5(2Η,η)，3·4-3·2(2Η,祖） 本紙張尺度適用中國國家標準（CNS ) Α4規格（2ί〇Χ 297公釐） 200 3 9 3 3 1 523506 A 7 B7 五、發明説明（20]) 管）fe例34 4-[2-[Ν-(1,3-二甲氧基丙-2-基）-苯磺醯胺基]-5-三氟甲 基苯氧甲基]苯甲酸Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Use 4- [2- [Ν- (1,3-dihydroxyprop-2-yl) -benzenesulfonamide Methyl] -5 -trifluoromethylphenoxymethyl] benzoate (synthesized from Example 32), following the same procedure as in Example 2, the title compound with the following physical data was obtained. TLC: Rf 0.51 (ethyl acetate: acetic acid = 99: 1); NMR: S8.13 (2H, d, J = 8.4Hz), 7.8-7.7 (2H, m), 7 · 6-7 · 2 (8H , m), 5.17 (lH, d, J = 11.4Hz), 5.08 (lH, d, J = 11.4Hz), 4.5-5-4 · 3 (1Η, ιη), 3.6 · 3.5 · 5 (2Η , η), 3 · 4-3 · 2 (2Η, ancestor) The paper size applies to the Chinese National Standard (CNS) A4 specification (2ί〇 × 297 mm) 200 3 9 3 3 1 523506 A 7 B7 V. Description of the invention (20) Tube) Example 34 4- [2- [N- (1,3-Dimethoxyprop-2-yl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl ]benzoic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH 使用4-[2-[Ν-(1,3-二羥基丙-2-基）-苯磺醯胺基]-5-三氟甲基苯氧甲基]笨甲酸甲酯（由實施例32合成），依參 考例194實施例2之相同操作，得具下列物理數據之標題 化合物。 TLC: Rf 0.57(氯仿：甲醇=9:1); NMR: S8.18(2H,d,J = 8.2Hz), 7·8-7·7(2Η,πι), 7·63(2Η, d,J = 8.2Hz), 7·6-7·4(3Η,ιη), 7·3-7·2(3Η,πι), 5·18(2Η, s), 4.5~4.4(1Η,πι) , 3 . 7-3 . 6 (1Η , m) , 3-5-3.0( 3H,m), 3 · 09 (3Η , s) , 3.04 (3Η , s) 經濟部中央標準局員工消費合作社印製 參者例30 2-(Ν-異丙基-甲磺醯胺基）-5-三氟甲基苯基甲氧甲基醚COOH uses methyl 4- [2- [N- (1,3-dihydroxyprop-2-yl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzate (from the Examples 32 Synthesis), following the same procedure as in Example 2 of Reference Example 194, the title compound having the following physical data was obtained. TLC: Rf 0.57 (chloroform: methanol = 9: 1); NMR: S8.18 (2H, d, J = 8.2Hz), 7 · 8-7 · 7 (2Η, πι), 7.63 (2Η, d , J = 8.2Hz), 7 · 6-7 · 4 (3Η, ιη), 7 · 3-7 · 2 (3Η, π), 5.18 (2Η, s), 4.5 ~ 4.4 (1Η, π) , 3. 7-3. 6 (1Η, m), 3-5-3.0 (3H, m), 3.009 (3Η, s), 3.04 (3Η, s) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Reference Example 30 2- (N-isopropyl-methanesulfonylamino) -5-trifluoromethylphenylmethoxymethyl ether

F3C、 /〇Me 使用2 -胺基-5-三氟甲基苯基甲氧甲基醚及甲基氯， 依參考例24實施例17之相同操作，得具下列物理數據之 標題化合物。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 201 393 3 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（ 2 02) TLC: Rf 0.40(己烷：乙酸乙酯=2:1)。 參者例3 1 2-(N-異丙基-2-羥基己磺醯胺基）-5-三氟甲基苯基甲氧甲 基醚 〇、^〇MeF3C, / 〇Me Using 2-amino-5-trifluoromethylphenylmethoxymethyl ether and methyl chloride, following the same procedures as in Reference Example 24 and Example 17, the title compound having the following physical data was obtained. This paper size applies to China National Standard (CNS) A4 (210X 297 mm) 201 393 3 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (2 02) TLC: Rf 0.40 (hexane : Ethyl acetate = 2: 1). Reference Example 3 1 2- (N-Isopropyl-2-hydroxyhexylsulfonamido) -5-trifluoromethylphenylmethoxymethyl ether 〇, ^ 〇Me

OH 2-(N-異丙基-甲磺醢胺基）-5-三氟甲基苯基甲氧甲基 醚（135mg;由參考例30合成）之THF(3.0ml)溶液中，在氩 氣流下，添加六甲基磷釀胺（420^1),在-78υ下滴加正 丁基鋰（742// 1),授拌1.5小時。混合物中滴加正戊醛（ 102nig)之THF(l.Oml)溶液，搅拌30分鐘。反應混合物中加 水，K乙酸乙酯萃取、洗淨、乾燥及減壓濃縮。殘留物Μ 矽膠管柱層析法（己烷：乙酸乙酯=4:1)純化，得具下列物 理數據之標題化合物（69mg)。 TLC: Rf 0.49(己烷：乙酸乙酯=2:1)。 參者例32 2-(N-異丙基-1-己烯磺醢胺基）-5-三氟甲基苯基甲氧甲基 継 .OMe (請先閱讀背面之注意事項再填寫本頁)In a solution of OH 2- (N-isopropyl-methanesulfonylamino) -5-trifluoromethylphenylmethoxymethyl ether (135 mg; synthesized from Reference Example 30) in THF (3.0 ml), argon Under air flow, hexamethylphosphorylamine (420 ^ 1) was added, and n-butyllithium (742 // 1) was added dropwise under -78υ, and the mixture was stirred for 1.5 hours. A solution of n-valeraldehyde (102 nig) in THF (1.0 ml) was added dropwise to the mixture, and the mixture was stirred for 30 minutes. Water was added to the reaction mixture, extracted with ethyl acetate, washed, dried, and concentrated under reduced pressure. The residue M was purified by silica gel column chromatography (hexane: ethyl acetate = 4: 1) to obtain the title compound (69 mg) having the following physical data. TLC: Rf 0.49 (hexane: ethyl acetate = 2: 1). Participant Example 32 2- (N-Isopropyl-1-hexenesulfonamido) -5-trifluoromethylphenylmethoxymethylphosphonium.OMe (Please read the precautions on the back before filling this page )

NN

2-(N-異丙基-2-羥基己磺醯胺基）-5-三氟甲基苯基甲 氧甲基醚（160mg;由參考例31合成）之二氯甲烷（2.0ml)溶 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 202 3 9 3 3 1 523506 A7 B7 五、發明説明（ 20 3) 液中，在氩氣流及0¾下添加三乙胺（104iul)及甲基氯（ 35/il),攪拌10分鐘。混合物中添加1.5-二吖雙環[5.4.0 ]十一碳烯（134/il),室溫下搅拌2小時。反應混合物中添 加稀塩酸，Μ乙酸乙酯萃取、洗淨、乾燥及減壓濃縮。殘 留物Κ矽膠管柱層析法（己烷：乙酸乙酯=8:1)純化，得具 下列物理數據之標題化合物（140ing)。 TLC: Rf 0.37(己烷：乙酸乙酯=3:1)。 管施例35 4-[2-(N-異丙基-1-己烯磺醢胺基）-5-三氟甲基苯氧甲基] 苯甲酸 (請先閱讀背面之注意事項再填寫本頁)2- (N-isopropyl-2-hydroxyhexylsulfonamido) -5-trifluoromethylphenylmethoxymethyl ether (160 mg; synthesized from Reference Example 31) in dichloromethane (2.0 ml) This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) 202 3 9 3 3 1 523506 A7 B7 V. Description of the invention (20 3) In the liquid, add triethylamine (104iul) under argon gas flow and 0¾ And methyl chloride (35 / il), and stirred for 10 minutes. To the mixture was added 1.5-diacbicyclo [5.4.0] undecene (134 / il), and the mixture was stirred at room temperature for 2 hours. Dilute acetic acid was added to the reaction mixture, extracted with ethyl acetate, washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 8: 1) to obtain the title compound (140ing) having the following physical data. TLC: Rf 0.37 (hexane: ethyl acetate = 3: 1). Example 35 4- [2- (N-Isopropyl-1-hexenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling in this page)

經濟部中央標準局員工消費合作社印製 使用2- (N -異丙基-1-己烯磺釀胺基）-5 -三氟甲基苯基 甲氧甲基醚（由參考例32合成），依參考例23*&gt;參考例6 4 實施例2之相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.44(氯仿：甲醇··乙酸=100:5:1); HMR： 58.19(2H,d,J=8-2Hz), 7.62(2H,d,J=8.2Hz), 7.22-7.45(3H,m), 6.68(lH,td,J=7*0,i5.0Hz), 6·09(1ΗPrinted using 2- (N-isopropyl-1-hexenesulfonylamino) -5-trifluoromethylphenylmethoxymethyl ether (synthesized from Reference Example 32) by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs Following the same procedures as in Reference Example 23 * &gt; Reference Example 6 4 and Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.44 (chloroform: methanol · acetic acid = 100: 5: 1); HMR: 58.19 (2H, d, J = 8-2Hz), 7.62 (2H, d, J = 8.2Hz), 7.22-7.45 ( 3H, m), 6.68 (lH, td, J = 7 * 0, i5.0Hz), 6.09 (1Η

,td,J=l-4,15*0Hz), 5.19(2H,s), 4.15(lH,m), 1.97(2H ,ia), 1.16_1.40(7H,m), 1.03(3H,d,J = 6.8Hz)，0.86(3H, m ) 參者例33 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 203 3 933 1 523506 A7 B7 五、發明説明（20 5) 混合物K乙酸乙_稀釋、洗淨、乾燥及減壓濃縮，得具下 列物理數據之標題化合物（317ffig)。 TLC: Rf 0.56(己烷：乙酸乙酯=2:1); NMR： 58-ll(2H,d,J=8.6Hz), 7*73(lH,brd,J=9^0Hz), 7.47(2H,d,J=8.6Hz), 7,25(lH,m), 7.15(lH,d,J=1.4Hz) ,6.95(lH,brs), 5.21(2H,s), 3.95(3H,s), 3·54(1Η，ιη) ，1 · 5 3 - 2 · 1 6 ( 8 H ,班） 管渝例37 4-[2-(N-異丙基-環丙基磺醢胺基-5-三氟甲基苯氧甲基] 苯甲酸 (請先閱讀背面之注意事項再填寫本頁), td, J = l-4,15 * 0Hz), 5.19 (2H, s), 4.15 (lH, m), 1.97 (2H, ia), 1.16_1.40 (7H, m), 1.03 (3H, d , J = 6.8 Hz), 0.86 (3H, m) Participant Example 33 This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 203 3 933 1 523506 A7 B7 V. Description of the invention (20 5) The mixture was diluted with ethyl acetate, washed, dried, and concentrated under reduced pressure to obtain the title compound (317ffig) having the following physical data. TLC: Rf 0.56 (hexane: ethyl acetate = 2: 1); NMR: 58-ll (2H, d, J = 8.6Hz), 7 * 73 (lH, brd, J = 9 ^ 0Hz), 7.47 ( 2H, d, J = 8.6Hz), 7,25 (lH, m), 7.15 (lH, d, J = 1.4Hz), 6.95 (lH, brs), 5.21 (2H, s), 3.95 (3H, s ), 3.54 (1Η, ιη), 1.55 3-2 · 16 (8H, class) Guan Yu Example 37 4- [2- (N-isopropyl-cyclopropylsulfonamido- 5-trifluoromethylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

COOHCOOH

經滴部中央標準局員工消費合作社印製 使用4-(2-環戊基磺釀胺基-5-三氟甲基苯氧甲基）笨 甲酸甲酯（由實施例36合成），依實施例174實施例2之相 同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.40(氯仿：甲醇：乙酸=100:5:1); NHR： 58-17(2H,d,J=8.4Hz), 7.61(2H,d,J=8,4Hz), 7.38(lH,d,J=8.0Hz), 7,28(2H,m), 5*17(2H,s), 4.36( lH,sept,J = 6*6Hz), 3.51(lH,m), 1*84-2·10(3Η,贝）， 1·61-1·84(3Η,πι), 1·30-1.56(2Η,ιπ), 1·24(3Η·υ = 6·6Printed using 4- (2-Cyclopentylsulfonyl-5-trifluoromethylphenoxymethyl) benzylformate (synthesized from Example 36) printed by the Consumer Cooperative of the Central Standards Bureau of Didi Ministry. Example 174 By the same procedure as in Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.40 (chloroform: methanol: acetic acid = 100: 5: 1); NHR: 58-17 (2H, d, J = 8.4Hz), 7.61 (2H, d, J = 8,4Hz), 7.38 (lH , d, J = 8.0Hz), 7,28 (2H, m), 5 * 17 (2H, s), 4.36 (lH, sept, J = 6 * 6Hz), 3.51 (lH, m), 1 * 84 -2 · 10 (3Η, Bay), 1.6 · 1-1 · 84 (3Η, πι), 1.30-1.56 (2Η, ιπ), 1 · 24 (3Η · υ = 6 · 6

Hz) , 1 ·08 (3Η,d , J = 6 · 6Ηζ) 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 205 3933 1 523506 A7 B7 五、發明説明（206) 實施例 37 ( 1 )-37 (7 ) 使用對應化合物，依參考例334實施例36&quot;»實施例17 —實施例2之相同操作，得具下列物理數據之標題化合物 Ο 奮_俐3 7 ( 1 ) 4-[2-(N -異丙基-環己基磺釀胺基）-5 -三氟甲基苯氧甲基] 笨甲酸Hz), 1 · 08 (3Η, d, J = 6 · 6Ηζ) This paper size is applicable to China National Standard (CNS) A4 specification (210X 297 mm) 205 3933 1 523506 A7 B7 V. Description of the invention (206) Examples 37 (1) -37 (7) Using the corresponding compounds, following the same operation as in Reference Example 334, Example 36 &quot; »Example 17—Example 2, the title compound with the following physical data was obtained. Fen_Li 3 7 (1) 4- [2- (N -Isopropyl-cyclohexylsulfonylamino) -5 -trifluoromethylphenoxymethyl] stearic acid

T L C ： R f 0.27 (乙酸乙酯：己烷=1:1); NM R ： δ 8.1 7 (2Η, d, J=8Hz), 7.61 (2H, d, J-8Hz), 7.42 (1 H, d, J=8Hz), 7.28 (1 H, d, J=8Hz), 7.26 (1 H, s), 5.1 9 (2H, s), 4.32 (1 H, m), 2.88 (1 H, m), 2.25-2.04 (2H, m), 1.92-1.35 (5H, m), 1.30-0.60 (9H, m)〇 謇濂例3 7 ( 2 1 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 4-[2-(N-異丙基-環己基磺醢胺基）-5-甲基苯氧甲基]苯甲 酸TLC: R f 0.27 (ethyl acetate: hexane = 1: 1); NM R: δ 8.1 7 (2Η, d, J = 8Hz), 7.61 (2H, d, J-8Hz), 7.42 (1 H, d, J = 8Hz), 7.28 (1 H, d, J = 8Hz), 7.26 (1 H, s), 5.1 9 (2H, s), 4.32 (1 H, m), 2.88 (1 H, m) , 2.25-2.04 (2H, m), 1.92-1.35 (5H, m), 1.30-0.60 (9H, m). Example 3 7 (2 1 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read first Note on the back, please fill in this page) 4- [2- (N-Isopropyl-cyclohexylsulfonamido) -5-methylphenoxymethyl] benzoic acid

本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 206 3933 1 523506 A7 B7______ 五、發明説明（207) T L C ： R f 0.37 (氯仿：甲醇：乙酸=100:5:1); NMR ： 58.15 (2H, d, J=8.6Hz), 7.59 (2H,d, J=8.6Hz), 7.17 (1H, d, J=8.4Hz), (請先閱讀背面之注意事項再填寫本頁) 6.82 (2H, m), 5.13 (2H, s), 4.32 (1H, m), 2.88 (1H, tt, J=3.2, 1 2.0Hz), 2.35 (3H, s), 2.15 (2H, m), 1.36-1.90 (5H, m), 1.23 (3H, d, J=6.6Hz), 1.12 (3H, d, J=6.6Hz), 0.82 (1H, m)〇 奮施例3 7 (3J_ 4-[2-(卜異丙基-異丙基磺釀胺基卜三氟甲基苯氧甲基]This paper size applies to Chinese National Standard (CNS) A4 (210 X 297 mm) 206 3933 1 523506 A7 B7______ 5. Description of the invention (207) TLC: R f 0.37 (chloroform: methanol: acetic acid = 100: 5: 1) ; NMR: 58.15 (2H, d, J = 8.6Hz), 7.59 (2H, d, J = 8.6Hz), 7.17 (1H, d, J = 8.4Hz), (Please read the precautions on the back before filling in this Page) 6.82 (2H, m), 5.13 (2H, s), 4.32 (1H, m), 2.88 (1H, tt, J = 3.2, 1 2.0Hz), 2.35 (3H, s), 2.15 (2H, m ), 1.36-1.90 (5H, m), 1.23 (3H, d, J = 6.6Hz), 1.12 (3H, d, J = 6.6Hz), 0.82 (1H, m). Example 3 7 (3J_ 4 -[2- (Isopropyl-isopropylsulfonylaminotrifluoromethylphenoxymethyl]

丁 L C : R f 0.34 (氛仿：甲酵：乙酸=100:5:1); NM R ： δ 8.1 8 (2Η, d, J=8.4Hz), 7.60 (2H, d, J=8.4Hz), 7.42 (1 H, d, J=8.0Hz), 7,23_7.33 (2H, m)，5.17 (2H, s)，4.32 (1H，sept, J=6.6Hz), 3.17 (1H，七峯， J=7.0Hz)，1.32 (3H，d, J=7.0Hz)，1.25 (3H，d，J=6.6Hz)，1.1 9 (3H，d，J=7.0Hz)， 1.09 (3H, d, J=6.6Hz)〇 經濟部中央標準局員工消費合作社印製 4 7 3 例 m 奮 基 丙 異 - N /IV I 2 _-I I 4 酸 ΜDing LC: R f 0.34 (Aromatic imitation: Formazan: Acetic acid = 100: 5: 1); NM R: δ 8.1 8 (2Η, d, J = 8.4Hz), 7.60 (2H, d, J = 8.4Hz) , 7.42 (1 H, d, J = 8.0Hz), 7,23_7.33 (2H, m), 5.17 (2H, s), 4.32 (1H, sep, J = 6.6Hz), 3.17 (1H, seven peaks , J = 7.0Hz), 1.32 (3H, d, J = 7.0Hz), 1.25 (3H, d, J = 6.6Hz), 1.1 9 (3H, d, J = 7.0Hz), 1.09 (3H, d, J = 6.6Hz) 〇 Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 4 7 3 cases m Fenyl propylene isopropyl-N / IV I 2 _-II 4 Acid M

甲 苯 TJ 基 甲 氧 苯 基 Η &lt; 甲ο -ο 5 C 本纸張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 207 3933 1 523506 A 7 B7 五、發明説明（2 0 8) T L C ： R f 0.46 (氯仿：甲醇：乙酸=1 Ο Ο : 5 : 1 ); NMR ： 5 8.15 (2Η, d, J=8.2Hz), 7.57 (2H,d, J=8.2Hz), 7.16 (1H, d, J=8.4Hz), 6.81 (2H，m)，5.1 1 (2H，s), 4.31 (1H,七峯，J=6.6Hz), 3.16 (1H,七峯，J=6.8Hz)， 2.36 (3H, s), 1.31 (3H, d, J=6.8Hz), 1.23 (3H, d, J=6.6Hz), 1.18 (3H, d, J=6.6Hz), 1.08 (3H, d, J=6.8Hz)〇 奮输{锎3 7 ( 5 ) 4 - [2-(H-異丙基-異丙基磺醢胺基）-5-三氟甲基苯氧甲基] 桂皮酸Toluene TJ-based methoxyphenyl hydrazone &lt; A ο -ο 5 C This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 207 3933 1 523506 A 7 B7 V. Description of the invention (2 0 8 ) TLC: R f 0.46 (chloroform: methanol: acetic acid = 1 Ο Ο: 5: 1); NMR: 5 8.15 (2Η, d, J = 8.2Hz), 7.57 (2H, d, J = 8.2Hz), 7.16 (1H, d, J = 8.4Hz), 6.81 (2H, m), 5.1 1 (2H, s), 4.31 (1H, seven peaks, J = 6.6Hz), 3.16 (1H, seven peaks, J = 6.8Hz ), 2.36 (3H, s), 1.31 (3H, d, J = 6.8Hz), 1.23 (3H, d, J = 6.6Hz), 1.18 (3H, d, J = 6.6Hz), 1.08 (3H, d , J = 6.8Hz) 〇 Lost {锎 3 7 (5) 4-[2- (H-isopropyl-isopropylsulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid

丁 L C : R f 0.20 (乙酸乙酯：己烷=1:1); NMR ： 57.79 (1H,d, J=15Hz),7.61 (2H, d, J=8Hz), 7.50 (2H, d, J=8Hz), 7.40 (1H,d, J=8Hz), 7.34-7.20 (2H, m), 6.48 (1H, d, J=15Hz), 5.12 (2H, s), 4.31 (1H, m), 3.1 4 (1 H, m), 1.31 (3H, d, J=7Hz), 1.25 (3H, d, J=7Hz), 1.1 5 (3H, d, J=7Hz), 1.07 (3H, d, J=7Hz)〇 經濟部中央標準局員工消費合作社印製 窗濂俐3 7 ( 6 ) 4-[2-(N-異丙基-環戊基磺醯胺基）-5-三氟甲基苯氧甲基] 桂皮酸DLC: R f 0.20 (ethyl acetate: hexane = 1: 1); NMR: 57.79 (1H, d, J = 15Hz), 7.61 (2H, d, J = 8Hz), 7.50 (2H, d, J = 8Hz), 7.40 (1H, d, J = 8Hz), 7.34-7.20 (2H, m), 6.48 (1H, d, J = 15Hz), 5.12 (2H, s), 4.31 (1H, m), 3.1 4 (1 H, m), 1.31 (3H, d, J = 7Hz), 1.25 (3H, d, J = 7Hz), 1.1 5 (3H, d, J = 7Hz), 1.07 (3H, d, J = 7Hz) 〇 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 3 7 (6) 4- [2- (N-isopropyl-cyclopentylsulfonamido) -5-trifluoromethylphenoxy Methyl] cinnamic acid

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 208 (請先閱讀背面之注意事項再填寫本頁) 39331 523506 Α7 Β7 五、發明説明（2〇si) T L C : R f 0.24 (乙酸乙酯：己烷=1 : 1 ); NMR ： 5 7.80 (1H,d, J=15Hz), 7.61 (2H, d, J=8Hz), 7.53 (2H, d, J=8Hz), 7.38 (1H,d, J=8Hz), 7.30-7.22 (2H, m), 6.48 (1 H, d, J=1 5Hz), 5.13 (2H, s), 4.35 (1H, m), 3.49 (1H, m), 2.20-1.16 (11H, m), 1.07 (3H，d，J=7Hz)。 管廉例3 7 ( 7 ) 4-[2-(H-異丙基-環己基磺釀胺基卜5-三氟甲基苯氧甲基] 桂皮酸This paper size applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 208 (Please read the notes on the back before filling out this page) 39331 523506 Α7 Β7 V. Description of the invention (2〇si) TLC: R f 0.24 (Ethyl acetate: hexane = 1: 1); NMR: 5 7.80 (1H, d, J = 15Hz), 7.61 (2H, d, J = 8Hz), 7.53 (2H, d, J = 8Hz), 7.38 (1H, d, J = 8Hz), 7.30-7.22 (2H, m), 6.48 (1 H, d, J = 1 5Hz), 5.13 (2H, s), 4.35 (1H, m), 3.49 (1H, m), 2.20-1.16 (11H, m), 1.07 (3H, d, J = 7Hz). Guanlian Example 3 7 (7) 4- [2- (H-Isopropyl-cyclohexylsulfonylaminotrifluorobutane 5-trifluoromethylphenoxymethyl] cinnamic acid

T L C : R f 0.27 (乙酸乙酯：己烷=1:1); NMR ： 5 7.80 (1H,d, J=15Hz),7.61 (2H, d, J=8Hz), 7.52 (2H, d, J=8Hz), 7.41 (1H,d,J-8Hz), 7.34-7.20 (2H, m), 6.48 (1 H, d, J=15Hz), 5.13 (2H, s), 4.32 (1H, m), 2.87 (1H, m), 2.21-2.00 (2H, m), 1.90-1.34 (5H, m), 1.26 (3H, d, J=7Hz), 1.18-0.60 (6H, m)〇 參者例34 經濟部中央標準局員工消費合作社印製 4-(3-硝基-5-三氟甲基吡啶-2-基氧甲基）苯甲酸甲酯TLC: R f 0.27 (ethyl acetate: hexane = 1: 1); NMR: 5 7.80 (1H, d, J = 15Hz), 7.61 (2H, d, J = 8Hz), 7.52 (2H, d, J = 8Hz), 7.41 (1H, d, J-8Hz), 7.34-7.20 (2H, m), 6.48 (1 H, d, J = 15Hz), 5.13 (2H, s), 4.32 (1H, m), 2.87 (1H, m), 2.21-2.00 (2H, m), 1.90-1.34 (5H, m), 1.26 (3H, d, J = 7Hz), 1.18-0.60 (6H, m). Example 34 Economy Printing of 4- (3-nitro-5-trifluoromethylpyridin-2-yloxymethyl) benzoic acid methyl ester by the Consumer Cooperatives of the Ministry of Standards of the People's Republic of China

(請先閱讀背面之注意事項再填寫本頁) ， Γ Τ 、 F3c ^^N〇2 2 -羥基-3-硝基-5-三氟甲基吡啶（l.Og)之甲苯（10ml) 溶液中，在氩氣流下，添加4 -氯甲基苯甲酸甲酯（1.32g) 及氧化銀（1 . 23g),加熱回流18小時。反應混合物予Μ過 本紙張尺度適用中國國家標準（CNS ) Α4規格（210Χ 297公釐） 209 3933 1 523506 A7 B7 五、發明説明（2 1 0) 濾、濾液予以濃縮，殘留物Μ乙酸乙酯再結晶，得具下列 物理數據之標題化合物（982mg)。 TLC: Rf 0.34(己烷：乙酸乙醮=3:1)。 管_例38 4-(3 -苯磺醸胺基-5 -三氟甲基吡啶-2 -基氧甲基）苯甲酸(Please read the precautions on the back before filling in this page), Γ Τ 、 F3c ^^ N〇2 2-hydroxy-3-nitro-5-trifluoromethylpyridine (1.0g) in toluene (10ml) solution Under a stream of argon, methyl 4-chloromethylbenzoate (1.32 g) and silver oxide (1.23 g) were added, and the mixture was heated under reflux for 18 hours. The reaction mixture was passed through the paper. The Chinese standard (CNS) A4 size (210 × 297 mm) was applied. 209 3933 1 523506 A7 B7 V. Description of the invention (2 1 0) The filtrate and the filtrate were concentrated. The residue was ethyl acetate. Recrystallization gave the title compound (982 mg) with the following physical data. TLC: Rf 0.34 (hexane: acetamidine acetate = 3: 1). Tube_Example 38 4- (3-Benzenesulfonamido-5-trifluoromethylpyridin-2-yloxymethyl) benzoic acid

使用4-(3 -硝基-5-三氟甲基吡啶-2 -基氧甲基）笨甲酸 甲酯（由參考例34合成），依參考例12-»參考例2-&gt;實施例 2之相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.50(氯仿··甲醇：乙酸=100:5:1); NMR(DMS0-d6): S 12,94(lH,m), 10·46(1Η,πι), 8·33(1Η, m), 7.89(2H,d,J=8.4Hz), 7.85(lH,d,J=2.2Hz), 7.73( 2H,m), 7·43-7·65(3Η,πι), 7·36(2Η，υ = 8·4Ηζ)，5·33( 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 2H , s) 參者例35 4-[2-(N-甲氧甲氧羰甲基-苯磺醢胺基三氟甲基苯氧 甲基]苯甲酸甲氧甲酯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 210 393 3 1 523506 A7 B7 五、發明説明（211)Using 4- (3-nitro-5-trifluoromethylpyridin-2-yloxymethyl) benzylcarboxylate (synthesized from Reference Example 34), follow Reference Example 12- »Reference Example 2- &gt; Examples By the same operation as in 2, the title compound having the following physical data was obtained. TLC: Rf 0.50 (chloroform · methanol: acetic acid = 100: 5: 1); NMR (DMS0-d6): S 12,94 (lH, m), 10.46 (1Η, π), 8.33 (1Η , m), 7.89 (2H, d, J = 8.4Hz), 7.85 (lH, d, J = 2.2Hz), 7.73 (2H, m), 7.43-7 · 65 (3Η, πι), 7. · 36 (2Η, υ = 8. · 4Ηζ), 5.33 (Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 2H, s) Participant Example 35 4- [2 -(N-methoxymethoxycarbonylmethyl-benzenesulfonamidotrifluoromethylphenoxymethyl) benzoic acid methanoate This paper is applicable to Chinese National Standard (CNS) A4 (210X 297 mm) 210 393 3 1 523506 A7 B7 V. Description of the invention (211)

使用4-(2-苯磺醯胺基-5-三氟甲基苯氧甲基）苯甲酸 甲酯（由實施例15合成），依實施例174實施例2般相同操 作，所得之4-[2-(N-羧甲基-苯磺醢胺基）-5-三氟甲基苯 氧甲基]苯甲酸（446mg)溶於DMF(5ml),滴加甲氧甲基氯（ 160/il)及三乙胺（300jul),於室溫攪拌2小時。添加水， Μ乙酸乙酯萃取，洗淨、乾燥、過濾、濃縮，得具下列物 理數據之標題化合物（47 6 mg)。 TLC: Rf 0.20(己烷：乙酸乙酯=3:1)。 參者例36 4-[2-[N-(N,N-二甲基胺羰甲基）-苯磺釀胺基]-5-三氟甲 基苯氧甲基]笨甲酸甲氧甲酯 ^\^C〇〇\^〇Me 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 'N CONMe2 〇2S\^^ 4-[2-(N-甲氧甲氧羰甲基-苯磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸甲氧甲酯（476mg;由參考例35合成）之 THF(2ih1)溶液中，添加二甲胺（0.8ml),於室溫搅拌3天。 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 211 39 3 3 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（212) 蒸除溶劑，殘留物以矽膠管柱層析法（己烷：乙酸乙酯=2:1 41:1)純化，得具下列物理數據之標題化合物（290mg)。 TLC: Rf 0.26(己烷：乙酸乙酯=1:1)。 奮淪例39 4-[2-[N-(N,N-二甲基胺羰基甲基）-苯磺醢胺基]-5-三氟 甲基苯氧甲基]笨甲酸Using 4- (2-benzenesulfonamido-5-trifluoromethylphenoxymethyl) benzoate (synthesized from Example 15), the same operation as in Example 174 and Example 2 was performed, and the resulting 4- [2- (N-carboxymethyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid (446mg) was dissolved in DMF (5ml), and methoxymethyl chloride (160 / il) and triethylamine (300 jul), and stirred at room temperature for 2 hours. Water was added, and the mixture was extracted with ethyl acetate, washed, dried, filtered, and concentrated to obtain the title compound (47 6 mg) having the following physical data. TLC: Rf 0.20 (hexane: ethyl acetate = 3: 1). Participant Example 36 4- [2- [N- (N, N-dimethylaminocarbonylmethyl) -benzenesulfonylamino] -5-trifluoromethylphenoxymethyl] methoxymethyl benzoate ^ \ ^ C〇〇 \ ^ 〇Me Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 'N CONMe2 〇2S \ ^^ 4- [2- (N- 甲Oxymethoxycarbonylmethyl-benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] methoxybenzoate (476mg; synthesized from Reference Example 35) in THF (2ih1), add two Methylamine (0.8 ml) was stirred at room temperature for 3 days. This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 211 39 3 3 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (212) The solvent is removed by distillation Purification by silica gel column chromatography (hexane: ethyl acetate = 2: 1 41: 1) gave the title compound (290 mg) with the following physical data. TLC: Rf 0.26 (hexane: ethyl acetate = 1: 1). Example 40 4- [2- [N- (N, N-dimethylaminocarbonylmethyl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzamic acid

使用4-[2-[N-(N,H-二甲基胺羰基甲基）-苯磺醸胺基] -5-三氟甲基苯氧甲基]苯甲酸甲氧甲酯（由參考例36合成） ，依參考例23之相同操作，得具下列物理數據之標題化合 物。 TLC: Rf 0.24(乙酸乙酯）； NMR: δ8·10-8·06(2Η,πι), 7.71-6,64(3H,m), 7·55-7·47 7.42-7.10(6H,m), 4.94(2H,s)， 4.56(2H，s)， 3 · 04 (3H , s) , 2♦86 (3H , s) 參者例37 、 4-苯磺醯胺基-3-甲氧基苯甲酸甲酷 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 212 3 93 3 1 ---------- (請先閱讀背面之注意事項再填寫本頁)Using 4- [2- [N- (N, H-dimethylaminocarbonylmethyl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzoic acid methoxymethyl (from reference (Synthesis of Example 36) According to the same operation as in Reference Example 23, the title compound having the following physical data was obtained. TLC: Rf 0.24 (ethyl acetate); NMR: δ8 · 10-8 · 06 (2Η, πm), 7.71-6,64 (3H, m), 7.55-7 · 47 7.42-7.10 (6H, m ), 4.94 (2H, s), 4.56 (2H, s), 3.04 (3H, s), 2 ♦ 86 (3H, s) See Example 37, 4-benzenesulfonamido-3-methoxy Methyl Benzoate This paper is sized for Chinese National Standard (CNS) A4 (210X 297 mm) 212 3 93 3 1 ---------- (Please read the notes on the back before filling this page )

、1T 丨象 523506 A7 B7, 1T 丨 Elephant 523506 A7 B7

五、發明説明（21$V. Description of the invention (21 $

NH 02S 使用4-硝基-3-羥基苯甲酸，依參考例64參考例124 參考例2之相同操作，得具下列物理數據之標題化合物。 TLC: Rf 0.12(己烷：乙酸乙酯=3:1) 參者例38 1-甲基-1-(4-苯磺醢胺基-3-甲氧基笨基）乙醇 (請先閲讀背面之注意事項再填寫本頁)NH 02S uses 4-nitro-3-hydroxybenzoic acid in the same manner as in Reference Example 64, Reference Example 124, and Reference Example 2 to obtain the title compound with the following physical data. TLC: Rf 0.12 (hexane: ethyl acetate = 3: 1) See Example 38 1-methyl-1- (4-benzenesulfonamido-3-methoxybenzyl) ethanol (please read the back first) (Notes for filling in this page)

經濟部中央標準局員工消費合作社印製 4-苯磺醯胺基-3-甲氧基苯甲酸甲酯（3.2g;由參考例 37合成）之THF(50ib1)懸浮液中，在-65υΤ滴加甲基鋰之 乙醚（38.8ml)歷時3小時，攪拌下溫度升至5¾。反應混合 物中添加稀塩酸調成中性後，Μ乙酸乙酯萃取。有機層予 Μ洗淨、乾煉及濃縮，得具下列物理數據之標題化合物。 T L C : R f (Κ 1 8 (己烷：乙酸乙酯=1 : 1) 參者例39 1-甲基-1-[4-(Ν-乙酿基-苯磺醯胺基）-3-甲氧苯基]乙醇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 213 39 3 3 1 523506 A7 B7 五、發明説明（214)In the THF (50ib1) suspension of methyl 4-benzenesulfonamido-3-methoxybenzoate (3.2g; synthesized from Reference Example 37) printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs at -65υΤ Drop Add methyl lithium diethyl ether (38.8ml) over 3 hours, and the temperature rose to 5¾ with stirring. The reaction mixture was neutralized by adding dilute acetic acid, and extracted with ethyl acetate. The organic layer was washed, dried and concentrated to obtain the title compound with the following physical data. TLC: R f (K 1 8 (hexane: ethyl acetate = 1: 1) Reference Example 39 1-Methyl-1- [4- (N-Ethyl-benzenesulfonylamino) -3- Methoxyphenyl] ethanol This paper is sized to the Chinese National Standard (CNS) A4 (210X 297 mm) 213 39 3 3 1 523506 A7 B7 V. Description of the invention (214)

1-甲基-1-(4-笨磺醸胺基-3-甲氧基苯基）乙醇（2.65g ;由參考例38合成）之二氯甲烷（15ml)溶液中添加乙酸酐（ 3.05ml)及三乙胺（4.60ml),於室溫攪拌一夜。蒸除溶劑 後，殘留物以矽膠管柱層析法（己烷：乙酸乙酯=3:4)純化· 得具下列物理數據之標題化合物（2.33g)。 TLC: Rf 0.19(己烷：乙酸乙酯=1:1) 參者例40 2-(H-乙酿基-笨磺酿胺基）-5-異丙基苯基甲醚To a solution of 1-methyl-1- (4-benzylsulfonylamino-3-methoxyphenyl) ethanol (2.65 g; synthesized from Reference Example 38) in dichloromethane (15 ml) was added acetic anhydride (3.05 ml ) And triethylamine (4.60ml), and stirred at room temperature overnight. After the solvent was distilled off, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 4). The title compound (2.33 g) having the following physical data was obtained. TLC: Rf 0.19 (hexane: ethyl acetate = 1: 1) Reference Example 40 2- (H-Ethyl-benzylsulfonylamino) -5-isopropylphenyl methyl ether

經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 1-甲基-1-[4-(Ν-乙醸基-笨磺醸胺基）-3-甲氧基笨基 ]乙醇（2.50g;由參考例39合成）之二氯甲烷（l〇al)溶液中 ，在0¾下加入三氯乙酸（1〇®1)及氫化三乙基矽烷（3·3π1) ,室溫下攪拌1小時。小心地將反應混合物加至飽和碳酸 氫納中，Κ乙酸乙酯萃取。有機層洗淨、乾燥並濃縮。殘 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 214 39 3 3 1 523506 A7 B7 五、發明説明（2 1 9 留物Μ矽膠管柱層析法（己烷：乙酸乙酿=3:1)純化，得具 下列物理數據之標題化合物（2.33g)。 TLC: Rf 0.24(己烷·•乙酸乙酯=1:1) 參者例41 2-(N-乙醯基-苯磺醢胺基）-5-異丙基酚Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) 1-methyl-1- [4- (N-ethylfluorenyl-benzylsulfonylamino) -3-methyl Oxybenzyl] ethanol (2.50g; synthesized from Reference Example 39) in dichloromethane (10al), trichloroacetic acid (10® 1) and hydrogenated triethylsilane (3 · 3π1), and stirred at room temperature for 1 hour. The reaction mixture was carefully added to saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed, dried and concentrated. The paper size of the scraps is in accordance with Chinese National Standard (CNS) A4 (210X 297 mm) 214 39 3 3 1 523506 A7 B7 V. Description of the invention (2 1 9 Residue M Silica gel column chromatography (hexane: ethyl acetate) (= 3: 1) Purified to obtain the title compound (2.33 g) with the following physical data. TLC: Rf 0.24 (hexane · • ethyl acetate = 1: 1) See Example 41 2- (N-Ethylfluorenyl) -Benzenesulfonylamino) -5-isopropylphenol

2-(N-乙醢基-笨磺醸胺基）-5-異丙基笨基甲醚（2.28g ;由參考例40合成）之二氛甲烷（15ml)溶液中，在0¾下添 加三溴化硼（1 . 3 6 1 ),在1 0 C搅拌5小時。反應混合物注 入冰水中，Μ乙酸乙酯萃取。有機曆洗淨、乾燥、濃縮。 殘留物Μ矽膠管柱層析法（苯：乙酸乙酯= 23:2)純化，於 乙酸乙酯-己烷之混合液中再結晶，得具下列物理數據之 標題化合物（1 · 5 5 g )。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) TLC: Rf 0.24(苯：乙酸乙簾=9:1) 參者例42 4-[2-(N-乙釀基-苯磺醸胺基）-5-異丙基'苯氧甲基]苯甲酸 甲酷 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 215 3 93 3 1 523506 A7 B7 五、發明説明（21In a solution of 2- (N-ethylammonium-benzylsulfonylamino) -5-isopropylbenzyl methyl ether (2.28g; synthesized from Reference Example 40) in methane (15ml), add three at 0¾ Boron bromide (1.3 6 1) was stirred at 10 C for 5 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate. Organic calendar is washed, dried and concentrated. The residue M was purified by silica gel column chromatography (benzene: ethyl acetate = 23: 2) and recrystallized from a mixed solution of ethyl acetate-hexane to obtain the title compound (1.55 g with the following physical data) ). Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the notes on the back before filling this page) TLC: Rf 0.24 (benzene: ethyl acetate = 9: 1) Participant Example 42 4- [2- (N- Ethyl-benzenesulfonylamino) -5-isopropyl'phenoxymethyl] benzoic acid This paper is sized for the Chinese National Standard (CNS) A4 (210X297 mm) 215 3 93 3 1 523506 A7 B7 V. Description of Invention (21

02S COOMe02S COOMe

使用2-(N-乙醢基-苯磺醢胺基）-5-異丙基酚（1.50g; 由參考例41合成），依參考例6之相同操作，得具下列物理 數據之標題化合物（2.22g)。 TLC: Rf 0.24(己烷：乙酸乙酯=7:3) 參者例43 4-(苯磺醢胺基）-3-甲氧基苯甲醇 〇MeUsing 2- (N-ethylfluorenyl-benzenesulfonylamino) -5-isopropylphenol (1.50 g; synthesized from Reference Example 41) and following the same procedure as in Reference Example 6, the title compound having the following physical data was obtained (2.22g). TLC: Rf 0.24 (hexane: ethyl acetate = 7: 3) Reference Example 43 4- (benzenesulfonamido) -3-methoxybenzyl alcohol 〇Me

NH 02S 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 在氩氣流下，使4-苯磺醯胺基-3-甲氧基苯甲酸甲酯 1.5g;由參考例37合成）之THF(90ml)溶液冷却至- 781C, 滴加氫化、二異丁基鋁（1.0M)之己烷（22 a 1)溶液。在-78 υ攪拌4小時，升溫至室溫後，Μ乙醚（l〇〇ml)稀釋，滴加 飽和硫酸鈉水溶液（1.5al),攪拌30分鐘，乾燥、過濾並 濃縮，得具下列物理數據之標題化合物（1.5g)。 TLC: Rf 0.31(乙酸乙酯：己烷=2:1) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 216 3933 1 523506 A7 B7五、發明説明（217) 參者例44 4-苯磺醢胺基-3-甲氧基苯甲醛 〇NH 02S Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) Under argon flow, make 4-benzenesulfonylamino-3-methoxybenzoic acid methyl ester 1.5g ; The THF (90 ml) solution synthesized from Reference Example 37 was cooled to -781C, and a solution of hydrogenated, diisobutylaluminum (1.0M) in hexane (22 a 1) was added dropwise. Stir at -78 υ for 4 hours. After warming to room temperature, diethyl ether (100 ml) is diluted. A saturated sodium sulfate aqueous solution (1.5al) is added dropwise, stirred for 30 minutes, dried, filtered and concentrated to obtain the following physical data. The title compound (1.5 g). TLC: Rf 0.31 (ethyl acetate: hexane = 2: 1) This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 216 3933 1 523506 A7 B7 V. Description of the invention (217) Participant examples 44 4-benzenesulfonamido-3-methoxybenzaldehyde. 44

在氩氣流下，於含4 -苯磺醸胺基-3 -甲氧苯甲醇（522 mg;由參考例43合成）之二氯甲烷（15ml)溶液中，在室溫 下添加二氧化錳（3g)並攪拌1小時。反應結束後，過滤，濾液濃縮，得具下列物理數據之標題化合物（404mg)。 TLC: Rf 0.57(乙酸乙酯：己烷=3:2) 參者例45 1 -（4-苯磺醯胺基-3-甲氧基苯基）乙醇 OH -------衣-- (請先閲讀背面之注意事項再填寫本頁) 、11 經濟部中央標準局員工消費合作社印製 /〇ΜθUnder a stream of argon, in a dichloromethane (15 ml) solution containing 4-benzenesulfenylamino-3 -methoxybenzyl alcohol (522 mg; synthesized from Reference Example 43), manganese dioxide ( 3g) and stirred for 1 hour. After completion of the reaction, the mixture was filtered and the filtrate was concentrated to obtain the title compound (404 mg) having the following physical data. TLC: Rf 0.57 (ethyl acetate: hexane = 3: 2) Reference Example 45 1-(4-benzenesulfonamido-3-methoxyphenyl) ethanol OH ------- yi- -(Please read the notes on the back before filling out this page), 11 Printed by the Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs / 〇Μθ

氩氣流下，含4-笨磺醸胺基-3-甲氧基苯甲醛（400fflg; 由參考例44合成）之THF(lOal)溶液冷却至-78Ό,滴加甲 基鋰（1.0Μ)之乙醚（3.4ml)溶液，攪拌20分鐘。反應结束 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 217 393 3 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（218) 後，添加水及1N塩酸K終止反應，Μ乙酸乙_萃取3次。 有機層經洗淨、乾煉，Κ矽膠管柱曆析法（乙酸乙酯：己烷 = 1:1)純化，得具下列物理數據之標題化合物（421ag)。 TLC: Rf 0.34(乙酸乙酯·•己烷=3:2)n m m /ίο 4-(2-苯磺釀胺基-5-異丙基苯氧甲基）苯甲酸Under an argon gas stream, a THF (lOal) solution containing 4-benzylsulfonylamino-3-methoxybenzaldehyde (400fflg; synthesized from Reference Example 44) was cooled to -78 Torr, and methyl lithium (1.0M) was added dropwise. Diethyl ether (3.4 ml) solution, stirred for 20 minutes. At the end of the reaction, the paper size applies the Chinese National Standard (CNS) A4 specification (210X 297 mm) 217 393 3 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. After adding the description of the invention (218), add water and 1N The reaction was terminated by osmic acid K, and extracted 3 times with ethyl acetate. The organic layer was washed and dried, and purified by K silica gel column chromatography (ethyl acetate: hexane = 1: 1) to obtain the title compound (421ag) with the following physical data. TLC: Rf 0.34 (ethyl acetate • hexane = 3: 2) n m m / ί 4- (2-benzenesulfonylamino-5-isopropylphenoxymethyl) benzoic acid

使用4-[2-(N -乙醯基-苯磺醸胺基）-5 -異丙基苯氧甲 基]苯甲酸甲酯（2.00g;由參考例42合成），依實施例2相 同操作，得具下列物理數據之標題化合物（1.66g)。 TLC: Rf 0.49(氯仿··甲酵=4:1) NMR(DMS0-d6): δ 7.84(2H,d，J=8.5Hz), 7·79-7·53(5Η， 姐），7.41(2H，d,J=8.5Hz), 6.90(lH，d，J=8Hz)， 6·63(1Η， d,J=2Hz), 6.55(lH,dd,J=8及 2Hz), 4.82(2H,s), 2·72( lH,m) , 1.10(6H,d, J = 7Hz) 〈 管_例41 4 -（2-笨磺醢胺基-5-乙基苯氧基甲基）苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 218 3933 1 --------^^衣-- (請先閱讀背面之注意事項再填寫本頁) 、\u 口 · 523506 A7 B7 五、發明説明（219)4- [2- (N -Ethylfluorenyl-benzenesulfonamido) -5 -isopropylphenoxymethyl] benzoic acid methyl ester (2.00 g; synthesized from Reference Example 42) was used as in Example 2 By operation, the title compound (1.66 g) having the following physical data was obtained. TLC: Rf 0.49 (chloroform ·· formase = 4: 1) NMR (DMS0-d6): δ 7.84 (2H, d, J = 8.5Hz), 7.79-7 · 53 (5Η, sister), 7.41 ( 2H, d, J = 8.5Hz), 6.90 (lH, d, J = 8Hz), 6.63 (1Η, d, J = 2Hz), 6.55 (lH, dd, J = 8 and 2Hz), 4.82 (2H , s), 2.72 (lH, m), 1.10 (6H, d, J = 7Hz) <Tube_Example 41 4-(2-Bentylsulfonamido-5-ethylphenoxymethyl) benzene Formic acid paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 218 3933 1 -------- ^^ clothing-(Please read the precautions on the back before filling this page), \ U mouth · 523506 A7 B7 V. Description of the invention (219)

COOH (請先閲讀背面之注意事項再填寫本頁) 使用1-(4-苯磺醢胺基-3-甲氧笨基）乙醇（由參考例45 合成），依參考例404參考例394參考例414參考例6-&gt;實 施例2般操作，得具下列物理數據之標題化合物。 TLC: Rf 0.29(乙酸乙酯：己烷：乙酸=5:14:1) HMR (DHSO-de) ： δ 12·87 (1 Η , brs ) , 9 . 53 (1H , brs) , 7.83( 2H,d,J=8.5Hz), 7·78-7·50(5Η,π〇, 7.39(2H，d,J=8.0Hz) ,6.86(2H,d,J = 8*0Hz), 6.57 (1H , d , J = 2 . 0Hz) , 6 . 50 (1H , dd,J=8,2Hz), 4.82(2H,brs), 2.44(2H,q,J=7,5Hz), 1·08 (3H,t,J = 7 ♦ 5Hz) 謇_例42 4-(2-笨磺醢胺基-5-羥甲基苯氧甲基）笨甲酸 經濟部中央標準局員工消費合作社印製COOH (Please read the notes on the back before filling this page) Use 1- (4-benzenesulfonamido-3-methoxybenzyl) ethanol (synthesized from Reference Example 45), refer to Reference Example 404, Reference Example 394 Example 414 Refer to Example 6- &gt; As in Example 2, the title compound was obtained with the following physical data. TLC: Rf 0.29 (ethyl acetate: hexane: acetic acid = 5: 14: 1) HMR (DHSO-de): δ 12 · 87 (1 Η, brs), 9.53 (1H, brs), 7.83 (2H , d, J = 8.5Hz), 7.78-7 · 50 (5Η, π〇, 7.39 (2H, d, J = 8.0Hz), 6.86 (2H, d, J = 8 * 0Hz), 6.57 (1H , d, J = 2.0Hz), 6.50 (1H, dd, J = 8,2Hz), 4.82 (2H, brs), 2.44 (2H, q, J = 7,5Hz), 1.08 (3H , t, J = 7 ♦ 5Hz) 例 _Example 42 4- (2-Bensulfenylamino-5-hydroxymethylphenoxymethyl) Benzoic acid Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

HOHO

NHNH

.COOH 使用4-硝基-3-羥基苯甲酸甲酯，依參考例194參考 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 219 3933 1 523506 A7 B7 五、發明説明（22$ 例204參考例24參考例434參考例394參考例234參考 例6 —實施例2般操作，得具下列物理數據之標題化合物。 TLC: Rf 0.39(乙酸乙酯：己烷：乙酸=13:6:1) NMR (DMSO-de) ： δ 1 2 · 83 (1 Η , brs ) , 9.56(lH,s), 7.83( 2H,d,J = 8,5Hz), 7.78-7.50(5H,a), 7*38(2H,d,J = 8.5Hz) ,6.88(lH,d,J=8.0Hz),6.74(lH,s), 6.56(lH，d, J=8.0Hz), 5.10(lH,brt,J=5.5Hz), 4.83(2H,s), 4.34( 2H,d,J = 5 . 5Hz) 參者例46 4-氯-2-羥基苯甲酸甲酯 。丨 ^&quot;^^COOMe 含4 -氯-2 -羥基苯甲酸（5.0g)之乙醚（50πι1)溶液在〇υ 下，添加重氮甲烷之乙醚溶液直至反應完全。反應混合物 經減壓濃縮，殘留物Κ矽膠管程層析法（己烷：乙酸乙酯= 4:1)純化，得具下列物理數據之標題化合物（5. 4g)。 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) TLC: Rf 0.60(己烷：乙酸乙酯=2:1) 參者例47 2-羥甲基-5-氯酚 、 氫化鋰鋁（l.lg)之THF(50ml)溶液在氩氣中，在（^下 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 220 3 93 3 1 523506 Α7 Β7 五、發明説明（221) 滴加含4-氯-2-羥基苯甲酸甲酯（5.38g;由參考例46合成） 之THF(50ml)溶液，上升至室溫並攪拌30分鐘。反應混合 物中加水，Μ乙醚-乙酸乙_混合液萃取，洗淨、乾燥及 減壓濃縮。殘留物Μ己烷-乙酸乙酯之混合液再結晶，得 具下列物理數據之標題化合物（3.92g)。 TLC: Rf 0.60(己烷：乙酸乙酯=1:1) 參者例48 4 -（2-甲磺醢氧基甲基-5-氯苯氧甲基）笨甲酸甲酷 COOMe 使用2-羥甲基-5-氯酚（由參考例47合成），依參考例 6-&gt;參考例8般操作，得具下列物理數據之標題化合物。 TLC: Rf 0·60(笨：丙 _=9:1) 參者例49 4-(2-叠氮甲基-5-氯苯氧甲基）苯甲酸甲酯 經濟部中央標準局員工消費合作社印製.COOH uses methyl 4-nitro-3-hydroxybenzoate. Refer to Reference Example 194. This paper size applies Chinese National Standard (CNS) A4 (210X 297 mm). 219 3933 1 523506 A7 B7. 5. Description of the invention ( 22 $ Example 204 Reference Example 24 Reference Example 434 Reference Example 394 Reference Example 234 Reference Example 6—Example 2 was performed to obtain the title compound with the following physical data. TLC: Rf 0.39 (ethyl acetate: hexane: acetic acid = 13 : 6: 1) NMR (DMSO-de): δ 1 2 · 83 (1 Η, brs), 9.56 (lH, s), 7.83 (2H, d, J = 8,5Hz), 7.78-7.50 (5H, a), 7 * 38 (2H, d, J = 8.5Hz), 6.88 (lH, d, J = 8.0Hz), 6.74 (lH, s), 6.56 (lH, d, J = 8.0Hz), 5.10 ( lH, brt, J = 5.5Hz), 4.83 (2H, s), 4.34 (2H, d, J = 5.5Hz) Reference Example 46 Methyl 4-chloro-2-hydroxybenzoate. ^ &quot; ^ ^ COOMe diethyl ether (50πι1) solution containing 4-chloro-2-hydroxybenzoic acid (5.0g) at 0 °, add diethyl ether ether solution until the reaction is complete. The reaction mixture is concentrated under reduced pressure, and the residue is a silicone tube. Purification by process chromatography (hexane: ethyl acetate = 4: 1) to obtain the title compound (5.4 g) with the following physical data. Member of the Central Standards Bureau, Ministry of Economic Affairs Printed by a consumer cooperative (please read the precautions on the back before filling this page) TLC: Rf 0.60 (hexane: ethyl acetate = 2: 1) Participant Example 47 2-hydroxymethyl-5-chlorophenol, lithium hydride Aluminum (l.lg) in THF (50ml) solution in argon, the paper size applies to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 220 3 93 3 1 523506 Α7 Β7 V. Invention Explanation (221) A solution of methyl 4-chloro-2-hydroxybenzoate (5.38 g; synthesized from Reference Example 46) in THF (50 ml) was added dropwise, and the mixture was warmed to room temperature and stirred for 30 minutes. Water was added to the reaction mixture. Diethyl ether-ethyl acetate mixture was extracted, washed, dried and concentrated under reduced pressure. The residue hexane-ethyl acetate mixture was recrystallized to obtain the title compound (3.92 g) with the following physical data. TLC: Rf 0.60 (Hexane: ethyl acetate = 1: 1) Refer to Example 48 4-(2-Methanesulfonyloxymethyl-5-chlorophenoxymethyl) methylcarbamate COOMe Use 2-hydroxymethyl-5 -Chlorophenol (synthesized from Reference Example 47), following the procedure of Reference Example 6-> Reference Example 8, the title compound having the following physical data was obtained. TLC: Rf 0 · 60 (Stupid: C_ = 9: 1) Participant Example 49 4- (2-Azidemethyl-5-chlorophenoxymethyl) benzoic acid methyl ester Consumer Consumption Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Print

(請先閲讀背面之注意事項再填寫本頁) COOMe 4-(2-甲磺醯氧基甲基-5-氯苯氧甲基）笨甲酸甲酯（ 628mg;由參考例48合成）之DMF(5.0ml)溶液在氨氣流下添 加叠氮化納（5 30mg),於60C攪拌40分鐘。反應混合物Μ 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 221 39 33 1 523506 A7 B7 五、發明説明（22 2) 乙酸乙酯稀釋，K矽藻土過濉不純物，濾液經洗淨、乾燥 及減壓濃縮，殘留物Μ矽膠管柱層析法（己烷：乙酸乙酯= 10:1)純化，得具下列物理數據之標題化合物（404ag)。 TLC: Rf 0,56(己烷：乙酸乙酯=4:1) 參者例50 4-(2-胺甲基-5-氯苯氧甲基）苯甲酸甲酯 COOMe (請先閱讀背面之注意事項再填寫本頁) rr(Please read the notes on the back before filling this page) COOMe DMF of 4- (2-Methanesulfonyloxymethyl-5-chlorophenoxymethyl) benzylformate (628mg; synthesized from Reference Example 48) (5.0ml) Sodium azide (5 30mg) was added to the solution under an ammonia stream, and the mixture was stirred at 60C for 40 minutes. Reaction mixture M This paper size is in accordance with Chinese National Standard (CNS) A4 specification (210X 297 mm) 221 39 33 1 523506 A7 B7 V. Description of the invention (22 2) Ethyl acetate dilution, K diatomaceous earth impure impurities, filtrate After washing, drying and concentration under reduced pressure, the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1) to obtain the title compound (404ag) having the following physical data. TLC: Rf 0,56 (hexane: ethyl acetate = 4: 1) Participant Example 50 4- (2-Aminomethyl-5-chlorophenoxymethyl) benzoate COOMe (Please read the (Please fill in this page again for attention) rr

NH2 4-(2-叠氮甲基-5-氯苯氧甲基）笨甲酸甲酯（389iag; 由參考例49合成）之THFU.Oul)溶液在室溫下添加三苯磷 46 2 mg),携拌3小時後，添加水，攪拌15小時。反應混合 物經減壓澹縮，殘留物以矽膠管柱層析法（氯仿：甲醇= 50 :1410:1)純化，得具下列物理數據之標題化合物（ 3 3 9 m g ) 〇 几(：：1^0,22(氯仿：甲醇=10:1) 經濟部中央標準局員工消費合作社印製 啻_例43 4-(2-苯磺酿胺基甲基-5-氯苯氧甲基）笨甲酸A solution of 4- (2-azidomethyl-5-chlorophenoxymethyl) benzyl carboxylate (389iag; synthesized from Reference Example 49) in THF (THF 2 .Oul) was added at room temperature to triphenylphosphine 46 2 mg) After stirring for 3 hours, add water and stir for 15 hours. The reaction mixture was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: methanol = 50: 1410: 1) to obtain the title compound (339 mg) with the following physical data. 〇 (:: 1 ^ 0,22 (Chloroform: methanol = 10: 1) Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs_Example 43 4- (2-benzenesulfonylaminomethyl-5-chlorophenoxymethyl) stearic acid

.COOH r τγ 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 222 3933 1 523506 A7 B7 五、發明説明（223) 使用4-(2-胺甲基-5-氯苯氧甲基）苯甲酸甲酯（由參考 例50合成），依參考例實施例2般操作，得具下列物理 數據之標題化合物。 TLC: Rf 0.49(氯仿：甲醇：乙酸=100:5:1) NMR(DHSO-de) ： δ 7 . 94 ( 2 Η , d , J = 8.0 Ηζ) , 7.77(2H,m), 7·45-7·70(5Η,ιη), 7·25(1Η,υ = 8·2Ηζ), 7.05(lH,d,J = 18Hz), 6.94(lH，dd,J = l8,8.2Hz), 5.20(2H，s), 4·00 (2Η , s) 管）fe例4 4 4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯氧甲基]苯基 丙炔酸 (請先閱讀背面之注意事項再填寫本頁).COOH r τγ This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) 222 3933 1 523506 A7 B7 V. Description of the invention (223) 4- (2-Aminomethyl-5-chlorophenoxymethyl) Methyl) benzoate (synthesized from Reference Example 50), following the procedure of Example 2 of Reference Example, the title compound having the following physical data was obtained. TLC: Rf 0.49 (chloroform: methanol: acetic acid = 100: 5: 1) NMR (DHSO-de): δ 7. 94 (2 Η, d, J = 8.0 Ηζ), 7.77 (2H, m), 7.45 -7 · 70 (5Η, ιη), 7.25 (1Η, υ = 8 · 2Ηζ), 7.05 (lH, d, J = 18Hz), 6.94 (lH, dd, J = 18,8.2Hz), 5.20 ( 2H, s), 4.00 (2Η, s) tube) fe 4 4 [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzene Propargylic acid (Please read the notes on the back before filling this page)

〇2S〇2S

經濟部中央標準局員工消費合作社印製 使用4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯氧 甲基]笨甲酸（由實施例1 8 ( 9 )合成），依參考例1 3 參考例 144參考例15-&gt;實施例2般操作，得具下列物理數據之標 題化合物。 TLC : Rf 0 . 32 (氯仿：甲醇=8 : 2) NMR： 57.80(2H,d,J=8Hz), 7.64(2H,d,J=8Hz), 7·68-7·26(8Η,ηι), 5.09(2H，s)，4·38(1Η,七峯，J = 6.5Hz) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 223 39 3 3 1 523506 A7 B7 五、發明説明（ 2 2 4) ,1 · 04 (6H，d，J = 6.5Hz) 啻_例45 4-[2-[2-(N -異丙基-苯磺醯胺基）-5 -三氟甲基苯]乙基]苯 甲酸Printed using 4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid (from Example 1 8 ( 9) Synthesis) According to Reference Example 1 3 Reference Example 144 Reference Example 15-> Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.32 (chloroform: methanol = 8: 2) NMR: 57.80 (2H, d, J = 8Hz), 7.64 (2H, d, J = 8Hz), 7.68-7 · 26 (8Η, ηι ), 5.09 (2H, s), 4.38 (1Η, seven peaks, J = 6.5Hz) This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) 223 39 3 3 1 523506 A7 B7 V. DESCRIPTION OF THE INVENTION (2 2 4), 1 · 04 (6H, d, J = 6.5Hz) 例 _ Example 45 4- [2- [2- (N -isopropyl-benzenesulfonamido) -5 -tri Fluoromethylbenzene] ethyl] benzoic acid

02S (請先閲讀背面之注意事項再填寫本頁)02S (Please read the notes on the back before filling this page)

COOHCOOH

使用4-[2-(2-第三丁氧羰胺基-5-三氟甲基苯基）-(EZ )-乙烯基]笨甲酸甲酯，依參考例204參考例234參考例2 4實施例174實ife例2般操作，得具下列物理數據之標題 化合物。 TLC: Rf 0.46 (氯仿：甲醇=9:1) NMR: 5 8.09(2H,d，J = 8.2Hz), 7·8-7·7(2Η,ιβ), 7·7-7·3( 7H,m), 6.88(lH,d,J=8.2Hz), 4·7-4.5(lH,m), 3·4-3·1( 經濟部中央標準局員工消費合作社印製 2H，m), 3.1，2.9(2H,m), 1.03(3H，d,J=6.8Hz), 0.93(3H, d,J=6·8Hz) 奮_例46 、 4-(2-苯磺醸胺基-4-氯笨氧甲基）苯甲醇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 224 3 9 3 3 1 523506 A7 B7 五、發明説明（2 2 5)Using methyl 4- [2- (2-third-butoxycarbonylamino-5-trifluoromethylphenyl)-(EZ) -vinyl] benzate, according to Reference Example 204 Reference Example 234 Reference Example 2 4 Example 174 was performed in the same manner as in Example 2 to obtain the title compound with the following physical data. TLC: Rf 0.46 (chloroform: methanol = 9: 1) NMR: 5 8.09 (2H, d, J = 8.2Hz), 7 · 8-7 · 7 (2Η, ιβ), 7 · 7-7 · 3 (7H , m), 6.88 (lH, d, J = 8.2Hz), 4 · 7-4.5 (lH, m), 3 · 4-3 · 1 (2H, m printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs), 3.1, 2.9 (2H, m), 1.03 (3H, d, J = 6.8Hz), 0.93 (3H, d, J = 6.8Hz) Fen_Example 46, 4- (2-benzenesulfonamido-4 -Chlorobenzyloxymethyl) benzyl alcohol This paper is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 224 3 9 3 3 1 523506 A7 B7 V. Description of the invention (2 2 5)

CICI

、〇H, 〇H

NH 〇2S 使用4-(2 -苯磺醯胺基-4 -氯苯氧甲基）苯甲酸甲酯（由 實施例7U)合成），依參考例43般操作，得具下列物理數 據之標題化合物。 TLC: Rf 0.24(己烷：乙酸乙酯=1:1) NMR: δ7·75(2Η,ιπ), 7.60(lH,d,J = 2.4Hz), 7·55(1Η,πι), 7.45(2H,m), 7-36(2H,d,J=8.0Hz), 7*13(2H,d,J=8.0Hz) ,7.03(lH,brs), 6*96(lH,dd,J=2.4,8.8Hz), 6.68(1H, d , J = 8 . 8Hz) , 4.86(2H,s), 4,73(2H，d,J = 5.8Hz), 1.74( 1H , t , J = 5·8Hz) 鬣.JS141 4-[N-[2-(4-氯苯磺醢胺基）-5-氯苯基]胺磺醯基]苯甲酸 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製NH 〇2S using methyl 4- (2-benzenesulfonamido-4-chlorophenoxymethyl) benzoate (synthesized from Example 7U), followed the procedure of Reference Example 43 to obtain the title with the following physical data Compound. TLC: Rf 0.24 (hexane: ethyl acetate = 1: 1) NMR: δ 7.75 (2Η, ιπ), 7.60 (lH, d, J = 2.4Hz), 7.55 (1Η, π), 7.45 ( 2H, m), 7-36 (2H, d, J = 8.0Hz), 7 * 13 (2H, d, J = 8.0Hz), 7.03 (lH, brs), 6 * 96 (lH, dd, J = 2.4, 8.8 Hz), 6.68 (1H, d, J = 8.8Hz), 4.86 (2H, s), 4,73 (2H, d, J = 5.8Hz), 1.74 (1H, t, J = 5 · 8Hz) I.JS141 4- [N- [2- (4-chlorobenzenesulfonylamino) -5-chlorophenyl] aminesulfonyl] benzoic acid (Please read the precautions on the back before filling this page) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

CI Κ、CI Κ,

XXXX

COOHCOOH

ΝΗ 02SΝΗ 02S

UCI 使用2-硝-4-氯苯胺，依參考例24參考例124參考例 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 225 39 33 1 523506 A7 B7 五、發明説明（2 26) 24實施例2般操作，得具下列物理數據之標題化合物。 1^(：:1^0*22(氯仿：甲醇：水=8:2:0,2) NHR(DHSO-de) ： δ 9.68(lH,br), 8 . 11 ( 2 Η , d , J = 8 . 4 Ηz), 7.84(2H,d，J=8.4Hz), 7.69(2H，d，J=8.8Hz), 7.62(2H,d, J=8.8Hz), 7.12(lH,dd,J=2.4及 8·4Ηζ), 7.02(lH，d, J = 2 . 4Hz) , 6 · 97 (1H，d,J = 8·4Hz) 管）例48 4-[2-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基笨基]-(E)-乙烯基]笨甲酸 (請先閱讀背面之注意事項再填寫本頁)UCI uses 2-nitro-4-chloroaniline, according to Reference Example 24, Reference Example 124, Reference Example The paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 225 39 33 1 523506 A7 B7 V. Description of the invention ( 2 26) Following the procedure of Example 2, the title compound having the following physical data was obtained. 1 ^ (:: 1 ^ 0 * 22 (chloroform: methanol: water = 8: 2: 0,2) NHR (DHSO-de): δ 9.68 (lH, br), 8. 11 (2 Η, d, J = 8. 4 Ηz), 7.84 (2H, d, J = 8.4Hz), 7.69 (2H, d, J = 8.8Hz), 7.62 (2H, d, J = 8.8Hz), 7.12 (lH, dd, J = 2.4 and 8. · 4Ηζ), 7.02 (lH, d, J = 2.4 Hz), 6 · 97 (1H, d, J = 8.4 Hz) tube) Example 48 4- [2- [2- (N- Isopropyl-benzenesulfonamido) -5-trifluoromethylbenzyl]-(E) -vinyl] benzic acid (Please read the precautions on the back before filling this page)

〇2Svv^^ 經濟部中央標準局員工消費合作社印製 使用4-[2-(2-第三丁氧羰胺基-5-三氟甲基苯基）-(E) -乙烯基]苯甲酸甲酯，依參考例234參考例2~&gt;實施例17 4實施例2般操作，得具下列物理數據之標題化合物。 TLC : Rf 0 · 45 (氯仿：甲醇=9 : 1) NHR： δ 8·2-8·0(3Η,m) , 7 * 9 - 7·7(2 Η ,m), 7.6 - 7.4 ( 7 Η,m) ,7·2-7.0(2H,m), 4.8-4.6(lH,m), l,08(3H,d,J=5.0Hz) ，1·05(3H,d,J=5·0Hz) 管淪例4 8 (1 ) 4-[2-[2-(H-異丙基苯磺醯胺基）-5-三氟甲基苯基]_(Z) - 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 226 3 93 3 1 523506 A7 B7 五、發明説明（ 2 27) 乙烯基]苯甲酸〇2Svv ^^ Printed by 4- [2- (2-Third-butoxycarbonylamino-5-trifluoromethylphenyl)-(E) -vinyl] benzoic acid The methyl ester was obtained in the same manner as in Reference Example 234, Reference Example 2 to &gt; Example 17 4 and Example 2, to obtain the title compound having the following physical data. TLC: Rf 0 · 45 (chloroform: methanol = 9: 1) NHR: δ 8 · 2-8 · 0 (3Η, m), 7 * 9-7 · 7 (2 Η, m), 7.6-7.4 (7 Η, m), 7.2-7.0 (2H, m), 4.8-4.6 (lH, m), l, 08 (3H, d, J = 5.0Hz), 1.05 (3H, d, J = 5 · 0Hz) Tube Example 4 8 (1) 4- [2- [2- (H-Isopropylbenzenesulfonamido) -5-trifluoromethylphenyl] _ (Z)-Applicable to this paper standard China National Standard (CNS) A4 specification (210X297 mm) 226 3 93 3 1 523506 A7 B7 V. Description of the invention (2 27) Vinyl] benzoic acid

COOH 02S 使用4-[2-(2-第三丁氧羰胺基-5-三氟甲基苯基）-(Z) -乙烯基]笨甲酸甲酯，依參考例234參考例24實施例17 4實施例2般操作，得具下列物理數據之標題化合物。 TLC: Rf 0.51(氯仿··甲醇=9:1) NHR： 57.97(2H,d,J=8.4Hz), 7.9-7.7(2H,m), 7.7-7.4( 5H,m), 7.31(2H,d,J = 8,4Hz), 7.1 -6·9(2Η，η〇, 77 (1Η d,J=12.4Hz), 4.7-4.5(lH,m), l*19(3H,d,J=6.6Hz), 1 · 04 (3H,d，J = 6♦6Hz) g _ 例 49 4-(2-苯甲醢胺基-5-氯苯氧甲基）苯甲酸 (請先閲讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製COOH 02S uses 4- [2- (2-tert-butoxycarbonylamino-5-trifluoromethylphenyl)-(Z) -vinyl] benzylformate, according to Reference Example 234 Reference Example 24 Example The title compound was obtained as in Example 2 with the following physical data. TLC: Rf 0.51 (chloroform · methanol = 9: 1) NHR: 57.97 (2H, d, J = 8.4Hz), 7.9-7.7 (2H, m), 7.7-7.4 (5H, m), 7.31 (2H, d, J = 8,4Hz), 7.1 -6 · 9 (2Η, η〇, 77 (1Η d, J = 12.4Hz), 4.7-4.5 (lH, m), l * 19 (3H, d, J = 6.6Hz), 1 · 04 (3H, d, J = 6 ♦ 6Hz) g _ Example 49 4- (2-benzylamino-5-chlorophenoxymethyl) benzoic acid (please read the note on the back first) Please fill in this page for further information.) Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

COOH 使用2 -硝基-5 -氯酚，依參考例64參考例124實施例 114實施例2般操作，得具下列物理數據之標題化合物。 本紙張尺度適用中國國家標準（CNS ) A4規格（2I0X 297公釐） 227 39 3 3 1 523506 A7 B7 _ 五、發明説明（2 2 8) TLC: Rf 0.51(氯仿：甲酵：乙酸=100:5:1) NMR (DHSO-de) ： δ 1 2 · 92 (1 Η , brs) , 9.64(lH,s), 7.94( 4H,m), 7.75(lH,d，J=8.6Hz), 7·47-7·68(5Η,πΟ, 7·23( lH,d,J=2-2Hz), 7.05(lH,dd,J=2-2,8.6Hz), 5-32(2H,s) g m m R 0-5 0(2) 使用4-(2-苯磺醸胺基-5-異丙基苯氧甲基）苯甲酸（由 實施例40合成）或4-(2-笨磺醢胺基-5-乙基苯氧甲基）苯甲 酸（由實施例41合成），依參考例實施例174實施例2般 操作，得具下列物理數據之標題化合物。 奮_例S0 4-[2-(N-異丙基-笨磺醢胺基）-5-異丙基苯氧甲基]苯甲酸COOH was treated with 2-nitro-5-chlorophenol according to Reference Example 64, Reference Example 124, Example 114, and Example 2 to obtain the title compound with the following physical data. This paper size applies the Chinese National Standard (CNS) A4 specification (2I0X 297 mm) 227 39 3 3 1 523506 A7 B7 _ V. Description of the invention (2 2 8) TLC: Rf 0.51 (chloroform: formazan: acetic acid = 100: 5: 1) NMR (DHSO-de): δ 1 2 · 92 (1 Η, brs), 9.64 (lH, s), 7.94 (4H, m), 7.75 (lH, d, J = 8.6Hz), 7 47-7 · 68 (5Η, πΟ, 7.23 (lH, d, J = 2-2Hz), 7.05 (lH, dd, J = 2-2,8.6Hz), 5-32 (2H, s) gmm R 0-5 0 (2) using 4- (2-benzenesulfonamido-5-isopropylphenoxymethyl) benzoic acid (synthesized from Example 40) or 4- (2-benzylsulfenamido) Methyl-5-ethylphenoxymethyl) benzoic acid (synthesized from Example 41), following the procedure of Reference Example Example 174 Example 2 to obtain the title compound with the following physical data. Fen_Example S0 4- [2 -(N-isopropyl-benzylsulfonylamino) -5-isopropylphenoxymethyl] benzoic acid

02S02S

COOH TLC ： R f 0.13 (氛仿：甲醇=19 : 1 ); ' 經濟部中央標準局員工消費合作社印m (請先閱讀背面之注意事項再填寫本頁) NMR (DMSO-d/) ： δ 7.85 (2Η, d, J=8Hz), 7.79-7.52(5H, m), 7.40 (2H, d, J=8Hz), 7.01 (1 H, d, J=8Hz), 6.73 (1 H, d, J=2Hz), 6.65 (1 H, dd, J=8 and 2Hz), 4.83 (2H, brs), 4.47 (1H, m), 2.80 (1H, m), 1.1 4 (6H, d, J=7Hz), 0.95 (6H, d, J=7Hz)〇 、 奮施例5 0 (1 ) 4-[2-(N-甲基-苯磺醢胺基）-5-異丙基苯氧甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 228 3 9 33 1 523506 A7 B7COOH TLC: R f 0.13 (Diffuse: Methanol = 19: 1); 'Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) NMR (DMSO-d /): δ 7.85 (2Η, d, J = 8Hz), 7.79-7.52 (5H, m), 7.40 (2H, d, J = 8Hz), 7.01 (1 H, d, J = 8Hz), 6.73 (1 H, d, J = 2Hz), 6.65 (1 H, dd, J = 8 and 2Hz), 4.83 (2H, brs), 4.47 (1H, m), 2.80 (1H, m), 1.1 4 (6H, d, J = 7Hz ), 0.95 (6H, d, J = 7Hz), Example 5 0 (1) 4- [2- (N-methyl-benzenesulfonamido) -5-isopropylphenoxymethyl] The size of benzoic acid paper is applicable to China National Standard (CNS) A4 (210X297 mm) 228 3 9 33 1 523506 A7 B7

COOHCOOH

五、發明説明（ 2 29) ja T L C ： R f 0.13 (氯仿：甲醇=19:1); NMR (DMSO-d^) ： δ 7.85 (2Η, d, J=8Hz), 7.76-7.53 (5H, m), 7.39 (2H, d, J=8Hz), 6.98 (1 H, d, J=8Hz), 6.77 (1 H, d, J=2Hz), 6.70 (1 H, dd, J=8 炎 2Hz), 4.78 (2H, brs), 3.33 (3H, s), 2.82 (1H, m), 1.15 (6H, d, J=7Hz)。 奮_例5 o m 4-[2-(N-異丙基-苯磺醸胺基）-5-乙基苯氧甲基]苯甲酸 (請先閱讀背面之注意事項再填寫本頁)V. Description of the invention (2 29) ja TLC: R f 0.13 (chloroform: methanol = 19: 1); NMR (DMSO-d ^): δ 7.85 (2Η, d, J = 8Hz), 7.76-7.53 (5H, m), 7.39 (2H, d, J = 8Hz), 6.98 (1 H, d, J = 8Hz), 6.77 (1 H, d, J = 2Hz), 6.70 (1 H, dd, J = 8) 2Hz ), 4.78 (2H, brs), 3.33 (3H, s), 2.82 (1H, m), 1.15 (6H, d, J = 7Hz). Fen_Example 5 o m 4- [2- (N-Isopropyl-benzenesulfonamido) -5-ethylphenoxymethyl] benzoic acid (Please read the precautions on the back before filling this page)

經濟部中央標準局員工消費合作社印製 NMR ：δ7.97 (2H, d, J=8.0Hz), 7.82-7.70 (2H, m), 7.62-7.32 (5H, m), 7.05 (1H, d, J=8.0Hz), 6.60 (1 H, dd, J=8, 1.5Hz), 6.53 (1 H, d, J=1.5Hz), 4.86 (2H, brs), 4.36 (1 H, qn, J=6.0Hz), 2.55 (2H, q, J=7.5Hz), 1.18 (3H, t, J=7.5Hz), 1.02 (6H, brd, J=6.0Hz)〇 &lt; 管濂例51 4 - [2-(N-異丙基-苯磺醢胺基）-5-三氟甲基苯氧甲基]桂皮 酸納塩 — 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 229 3933 1 523506 A7 B7 五、發明説明（ 2 3 0)Printed NMR by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs: δ7.97 (2H, d, J = 8.0Hz), 7.82-7.70 (2H, m), 7.62-7.32 (5H, m), 7.05 (1H, d, J = 8.0Hz), 6.60 (1 H, dd, J = 8, 1.5Hz), 6.53 (1 H, d, J = 1.5Hz), 4.86 (2H, brs), 4.36 (1 H, qn, J = 6.0Hz), 2.55 (2H, q, J = 7.5Hz), 1.18 (3H, t, J = 7.5Hz), 1.02 (6H, brd, J = 6.0Hz) 〇 Management Example 51 4-[2 -(N-Isopropyl-benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] naphthyl cinnamate — This paper size applies to China National Standard (CNS) A4 (210X297 mm) 229 3933 1 523506 A7 B7 V. Description of the invention (2 3 0)

4-[2-(N-異丙基-苯磺醢胺基）-5-三氟甲基苯氧甲基] 桂皮酸（425mg;由實施例18(40)合成）之甲醇（5ml)溶液中 ，添加2N氫氧化納（0.41ml),室溫下攢拌，與苯進行共沸 3次，得具下列物理數據之標題化合物（ 430iag)。 TLC: Rf 0·19(己烷：乙酸乙酯=1:1) NMR: 57.60(2H,d，J=7Hz), 7·40-6·97(11Η,π〇， 6.47( 1Η , d , J = 16Hz) , 4,62(2H,bs), 4·20-4.08(1Η,πι), 0 · 77 ( 6H,d,J=5Hz) g m m 52(1)-52(5) 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 使用4-(2-胺基-5-三氟甲基苯氧甲基）苯甲酸甲酯（由 參考例17合成）及對應之苯磺醸氯衍生物，依實施例44實 施例19(環戊基甲醇K異丙醇替代）《*&gt;實施例2般操作，得 具下列物理數據之標題化合物。 啻）fe 例 5 2 Π) 、 4-[2-(N-異丙基-4-丙氧基苯磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 230 39 3 3 1 523506 A7 B7 五、發明説明（231)4- [2- (N-Isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid (425mg; synthesized from Example 18 (40)) in methanol (5ml) 2N sodium hydroxide (0.41 ml) was added, and stirred at room temperature, and azeotroped with benzene three times to obtain the title compound (430iag) having the following physical data. TLC: Rf 0.19 (hexane: ethyl acetate = 1: 1) NMR: 57.60 (2H, d, J = 7 Hz), 7.40-6.97 (11Η, π〇, 6.47 (1Η, d, J = 16Hz), 4,62 (2H, bs), 4.20-4.08 (1Η, πι), 0 · 77 (6H, d, J = 5Hz) gmm 52 (1) -52 (5) Central Ministry of Economic Affairs Printed by the Standards Bureau ’s Consumer Cooperative (please read the notes on the back before filling this page) Use 4- (2-amino-5-trifluoromethylphenoxymethyl) benzoic acid methyl ester (Synthesized from Reference Example 17) ) And the corresponding benzylsulfonium chloride derivative, according to Example 44, Example 19 (replacement of cyclopentylmethanol K isopropanol) "* &gt; Example 2, the title compound with the following physical data was obtained. 啻) fe Example 5 2 Π), 4- [2- (N-isopropyl-4-propoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid This paper is applicable to China Standard (CNS) A4 specification (210X 297 mm) 230 39 3 3 1 523506 A7 B7 V. Description of the invention (231)

02S02S

COOHCOOH

OC3H7 TLC : R f 0·55 (氯仿：甲醇=9 : 1); NMR ： δ 8.16 (2Η, d, J=8.8Hz), 7.71 (2H, d, J=8.8Hz), 7.54 (2H, d, J=8.8HZ), 7.30-7.22 (3H, m), 6.80 (2H, d, J=8.8Hz), 5.1 4 (2H, s), 4.44-4.24 (1 H, m), 3.92 (2H, t, J=6.6Hz), 1.91-1.72 (2H, m), 1.14-0.98 (9H, m)〇 奮 Ife 例 5 2 ( 2 ) 4-[2-(N -異丙基-4 -乙硫基苯磺釀胺基）-5 -三氟甲基苯氧 甲基]苯甲酸OC3H7 TLC: R f 0 · 55 (chloroform: methanol = 9: 1); NMR: δ 8.16 (2Η, d, J = 8.8Hz), 7.71 (2H, d, J = 8.8Hz), 7.54 (2H, d , J = 8.8HZ), 7.30-7.22 (3H, m), 6.80 (2H, d, J = 8.8Hz), 5.1 4 (2H, s), 4.44-4.24 (1 H, m), 3.92 (2H, t, J = 6.6Hz), 1.91-1.72 (2H, m), 1.14-0.98 (9H, m). Example 5 2 (2) 4- [2- (N -isopropyl-4 -ethylsulfide) Benzenesulfonylamino) -5 -trifluoromethylphenoxymethyl] benzoic acid

02S02S

COOH (請先閱讀背面之注意事項再填寫本頁) 經濟部中央標準局員工消費合作社印製 &quot;SC2H5 丁 L C : R f 0.64 (氯仿：甲醇=9:1); NM R ： δ 8.17 (2H, d, J=8.4Hz), 7.66 (2H, d, J=8.4Hz), 7.53 (2H, d J=8.4Hz), .30-7.20 (3H, m), 7.16 (2H, d, J=8.4Hz), 5.12 (2H, s), 4.44-4.22 (1 H; m), 2.98 (2H,q, J=7.6Hz), 1.36 (3H, t, J=7.6Hz), 1.09 (3H, d, J=6.6Hz), 1.05 (3H, d, J=6.6Hz)〇 g嫵例5 2 ( 3) 4-[2-(N-異丙基-4 -甲硫基苯磺醢胺基）-5-三氟甲基苯氧 本紙張尺度適用中國國家標準（CNS ) A4規格（210X29?公釐） 231 3933 1 523506 A7 B7 五、發明説明（232) 甲基]苯甲酸COOH (Please read the notes on the back before filling this page) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs &quot; SC2H5 DLC: R f 0.64 (chloroform: methanol = 9: 1); NM R: δ 8.17 (2H , d, J = 8.4Hz), 7.66 (2H, d, J = 8.4Hz), 7.53 (2H, d J = 8.4Hz), .30-7.20 (3H, m), 7.16 (2H, d, J = 8.4Hz), 5.12 (2H, s), 4.44-4.22 (1 H; m), 2.98 (2H, q, J = 7.6Hz), 1.36 (3H, t, J = 7.6Hz), 1.09 (3H, d , J = 6.6Hz), 1.05 (3H, d, J = 6.6Hz) 〇g Example 5 2 (3) 4- [2- (N-isopropyl-4 -methylthiobenzenesulfonamido) -5-Trifluoromethylphenoxy This paper applies Chinese National Standard (CNS) A4 specifications (210X29? Mm) 231 3933 1 523506 A7 B7 V. Description of the invention (232) Methyl] benzoic acid

NM R ： δ 8.16 (2Η, d, J=8.4Hz), 7.67 (2H, d, J=8.4Hz), 7.52 (2H, d, J=8.4Hz), 7.30-7.20 (3H, m), 7.12 (2H, d, J=8.4Hz), 5.12 (2H, s), 4.46-4.24 (1 H, m), 2.48 (3H, s), 1.09 (3H, d, J=7.0Hz), 1.05 (3H, d, J=7.0Hz)〇 富濂例5 2 ( 4 ) 4-[2-(N -異丙基-4 -丁氧基苯磺酿胺基）-5 -三氟甲基苯氧 甲基]笨甲酸NM R: δ 8.16 (2Η, d, J = 8.4Hz), 7.67 (2H, d, J = 8.4Hz), 7.52 (2H, d, J = 8.4Hz), 7.30-7.20 (3H, m), 7.12 (2H, d, J = 8.4Hz), 5.12 (2H, s), 4.46-4.24 (1 H, m), 2.48 (3H, s), 1.09 (3H, d, J = 7.0Hz), 1.05 (3H , d, J = 7.0Hz). Rich example 5 2 (4) 4- [2- (N -isopropyl-4 -butoxybenzenesulfonylamino) -5 -trifluoromethylphenoxymethyl Methyl

02S02S

COOH 經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) 、〇c4h9 T L C ： R f 0.51 (氯仿•·甲醇=9 : 1 ); ' NMR ： δ 8.16 (2H, d, J=8.4Hz), 7.71 (2H, d, J=8.8Hz), 7.54 (2H, d, J=8.4Hz), 7.30-7.22 (3H, m), 6.79 (2H, d, J=8.8Hz), 5.14 (2H, s), 4.42-4.27 (1 H, m), 3.96 (2H, t, J=6.2Hz), 1.87-1.70 (2H, m), 1.60-1.40 (2H, m), 1.14-0.92 (9H, m)〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 232 3933 1 523506Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page), 〇c4h9 TLC: R f 0.51 (chloroform • · methanol = 9: 1); 'NMR: δ 8.16 (2H , d, J = 8.4Hz), 7.71 (2H, d, J = 8.8Hz), 7.54 (2H, d, J = 8.4Hz), 7.30-7.22 (3H, m), 6.79 (2H, d, J = 8.8Hz), 5.14 (2H, s), 4.42-4.27 (1 H, m), 3.96 (2H, t, J = 6.2Hz), 1.87-1.70 (2H, m), 1.60-1.40 (2H, m) , 1.14-0.92 (9H, m). This paper size is applicable to the Chinese National Standard (CNS) A4 specification (210X 297 mm) 232 3933 1 523506

A7 B7 五、發明説明（ 23 3) 奩_例52 (5) 4 - [2-(N-異丙基-4-異丙氧基苯磺醢胺基）-5-三氟甲基苯 氧甲基]苯甲酸 NMR ：δ 8.17(2H, d, J=8.0Hz), 7.71 (2H, d, J=8.8Hz), 7.56 (2H, d, J=8.0Hz), 7.30-7.22 (3H, m), 6.78 (2H, d, J=8.8Hz), 5.15 (2H, s), 4.62-4.50 (1 H, m), 4.40-4.23 (1H, m), 1.35 (6H, d, J=5.8Hz), 1.08 (3H, d, J=7.4Hz), 1.04 (3H, d, J=7.4Hz)〇 奮施例5 3 m - 5 3 m (請先閱讀背面之注意事項再填寫本頁) 用 使 酯 甲 酸 甲 苯 或 \n/ 成 合 成 合 7 1X 例 考 參 醛 基之 甲應 氧對 基苯用 甲基使 氧甲 7 ί本氟!2 例 氯三^ I - 施 5 5 I I 實 基基依 按按 &quot;&quot;»【 ΗΠΜ , 例由 考i 參 由 1 1X 酯例 甲施 酸實 甲-&gt; 苯&gt; 經濟部中央標準局員工消費合作社印製 物 合 化 題 標 之 據 數 Jc 理 物 列 下 具 得 作 操 般 2 例 施 實 基 胺 醯 甲 笨 讎 基 丁 異 酸 甲 苯 I-1 基 Ψ 氧 苯 氯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 233 3 93 3 1 523506 A7 B7 五、發明説明（ 2 34)A7 B7 V. Explanation of the invention (23 3) Example 52 (5) 4-[2- (N-isopropyl-4-isopropoxybenzenesulfonamido) -5-trifluoromethylphenoxy Methyl] benzoic acid NMR: δ 8.17 (2H, d, J = 8.0Hz), 7.71 (2H, d, J = 8.8Hz), 7.56 (2H, d, J = 8.0Hz), 7.30-7.22 (3H, m), 6.78 (2H, d, J = 8.8Hz), 5.15 (2H, s), 4.62-4.50 (1 H, m), 4.40-4.23 (1H, m), 1.35 (6H, d, J = 5.8 Hz), 1.08 (3H, d, J = 7.4Hz), 1.04 (3H, d, J = 7.4Hz) 0 Fen Example 5 3 m-5 3 m (Please read the precautions on the back before filling this page) Use the ester of formic acid toluene or \ n / to synthesize 7 1X Example of the aldehyde group of methyloxy-p-phenylbenzene. Use methyl to make oxygen methyl 7 Fluorine! 2 Examples of chlorotri ^ I-Shi 5 5 II Keyword press &quot; &quot; »[ΗΠΜ, example by test i reference by 1 1X ester example of acid application of real acid- &gt; benzene &gt; evidence for the title of the printed matter compound of the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Calculate the physical properties of Jc. 2 cases can be used as a practical example of stilbeneamine, methylbenzyl butyroisobutyric acid, toluene I-1 based, oxybenzene chloride. The paper size applies to Chinese National Standard (CNS) A4 specifications (210 X 297 mm) 233 3 93 3 1 523506 A7 B7 V. Description of the invention (2 34)

COOH TLC: Rf 0.53(氯仿：甲醇=5:1); NMR(CDCl3+l滴 CD30D): 5 8.08(2H,d,J=8Hz), 7·44-7·04 (8H,m), 6.94-6.80(lH,m), 6.73(lH,s), 5.03(lH,d,J= 13Hz), 4.82(lH,d，J=13Hz), 3.91(lH,dd,J=15.7Hz), 3*49(lH,dd,J = 15.7Hz), 2-10-1.60(lH,ia), 0 · 9 8 ( 6 H , d , J = 7Hz) 窖施例5 3 ( 2丄 4-[2-(N -異丙基-苯甲醸胺基）-5-三氟甲基苯氧甲基]苯甲 酸COOH TLC: Rf 0.53 (chloroform: methanol = 5: 1); NMR (CDCl3 + l drop CD30D): 5 8.08 (2H, d, J = 8Hz), 7.44-7 · 04 (8H, m), 6.94 -6.80 (lH, m), 6.73 (lH, s), 5.03 (lH, d, J = 13Hz), 4.82 (lH, d, J = 13Hz), 3.91 (lH, dd, J = 15.7Hz), 3 * 49 (lH, dd, J = 15.7Hz), 2-10-1.60 (lH, ia), 0 · 9 8 (6 H, d, J = 7Hz) Cell Example 5 3 (2 丄 4- (2 -(N -Isopropyl-benzylamido) -5-trifluoromethylphenoxymethyl] benzoic acid

COOHCOOH

經濟部中央標準局員工消費合作社印製 (請先閲讀背面之注意事項再填寫本頁) T L C ： R f 0.49 (氯仿：甲醇= 9:1); ) NMR ： δ 8.18 (2Η, d, J=8.4Hz), 7.52-7.35 (3H, m), 7.30-7.03 (6H, m), 7.02-6.92 (1H, m), 5.20-4.90 (2H, m), 4.90-4.70 (1H, m), 1.50-1.00 (6H, m)〇 管油{例5 3 ( 3 ) 4-[2-(N-異丙基-2-呋喃醯胺基）-5-三氟甲基苯氧甲基]苯 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 234 393 3 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（23 5) 甲酸Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) TLC: R f 0.49 (chloroform: methanol = 9: 1);) NMR: δ 8.18 (2Η, d, J = 8.4Hz), 7.52-7.35 (3H, m), 7.30-7.03 (6H, m), 7.02-6.92 (1H, m), 5.20-4.90 (2H, m), 4.90-4.70 (1H, m), 1.50 -1.00 (6H, m) 〇 Pipe oil {Example 5 3 (3) 4- [2- (N-isopropyl-2-furanamido) -5-trifluoromethylphenoxymethyl] benzene Paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 234 393 3 1 523506 A7 B7 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (23 5) Formic acid

COOH NMR ： δ 8.09 (2Η, d, J=7.8Hz), 7.43-7.22 (5H, m), 7.15 (1H, s), 6.25-6.20 (1H, m), 6.16-6.08 (1H, br), 5.20-4.84 (3H, m), 1.40-1.00 (6H, m)〇 啻淪例FU 4- (2-苯甲醢胺基COOH NMR: δ 8.09 (2Η, d, J = 7.8Hz), 7.43-7.22 (5H, m), 7.15 (1H, s), 6.25-6.20 (1H, m), 6.16-6.08 (1H, br), 5.20-4.84 (3H, m), 1.40-1.00 (6H, m). Examples of FU 4- (2-benzylamine)

氯苯甲醢胺基）苯甲酸 XOOHChlorobenzylamino) benzoic acid XOOH

使用2-硝基-5-氯苯甲醯氯（由參考例13合成），依實 施例11~&gt;參考例104實施例114實施例2般操作，得具下 列物理數據之標題化合物。 TLC: Rf 0.52(乙酸乙酯：己烷：乙酸= 7:12:1); NMR(DMSO-de)： 5 12*77(lH,brs), 1K3S(1H,s) 1H，s), 8*36(lH，d,J = 9.0Hz), 8·02-7·78(7Η，πι) lH,dd,J = 9.0,2.5Hz), 7·64-7·48(3Η,πι) g m m 55(1)-55(2) 使用2-硝基-5-氯苯甲醢氯（由參考例13合成），依實 10.85( 7.69( (請先閱讀背面之注意事項再填寫本頁) 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 235 39 3 3 1 523506Using 2-nitro-5-chlorobenzidine chloride (synthesized from Reference Example 13) and following the procedures of Examples 11 to &gt; Reference Example 104, Example 114, Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.52 (ethyl acetate: hexane: acetic acid = 7: 12: 1); NMR (DMSO-de): 5 12 * 77 (lH, brs), 1K3S (1H, s) 1H, s), 8 * 36 (lH, d, J = 9.0Hz), 8.02-7 · 78 (7Η, π) lH, dd, J = 9.0,2.5Hz), 7.64-7 · 48 (3Η, π) gmm 55 (1) -55 (2) Using 2-nitro-5-chlorobenzidine chloride (synthesized from Reference Example 13), according to the actual 10.85 (7.69 ((Please read the precautions on the back before filling this page)) Paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 235 39 3 3 1 523506

A7 B7____ 五、發明説明（ 2 36) 施例11 參考例10 參考例實施例2般操作，得具下列 物理數據之標題化合物。 管）ife 例 R R ( 11 4-[2-(2-睡吩基磺醢胺基）_5-氯笨甲醢胺基]苯甲酸 COOHA7 B7____ 5. Description of the Invention (2 36) Example 11 Reference Example 10 Reference Example Example 2 was carried out to obtain the title compound with the following physical data. Tube) ife case R R (11 4- [2- (2-Phenylsulfenamido) _5-chlorobenzylamido] benzoic acid COOH

T L C ： R f 0.18 (氯仿：甲醇= 9:1); NMR (DMSO-d/；&gt;) ： δ 12.73 (1 H, br), 10.68 (1 H, brs), 10.48 (1 H, brs), 7.93 (2H, d, J=8.8Hz), 7.87 (1H, dd, J=1.2 ^ 3.6Hz), 7.81 (1H, d, J=2.2Hz), 7.76 (2H,d, J=8.8Hz), 7.61-7.53 (2H, m), 7.41 (1H,d, J=8.8Hz), 7.05 (1H,dd, J=3.8 反 4.0Hz)o 管淪俐S fW 2 ) 4-(2-丁磺藤胺基-5-氯苯甲醸胺基）苯甲酸 (請先閱讀背面之注意事項再填寫本頁) ··· 經濟部中央標率局員工消費合作社印製TLC: R f 0.18 (chloroform: methanol = 9: 1); NMR (DMSO-d /; &gt;): δ 12.73 (1 H, br), 10.68 (1 H, brs), 10.48 (1 H, brs) , 7.93 (2H, d, J = 8.8Hz), 7.87 (1H, dd, J = 1.2 ^ 3.6Hz), 7.81 (1H, d, J = 2.2Hz), 7.76 (2H, d, J = 8.8Hz) , 7.61-7.53 (2H, m), 7.41 (1H, d, J = 8.8Hz), 7.05 (1H, dd, J = 3.8 inverse 4.0Hz) o tube SLi 2 f) 4- (2-butane Tengamido-5-chlorobenzylamino) benzoic acid (Please read the notes on the back before filling out this page) ··· Printed by the Employees' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

'NH'NH

COOH T L C ： R f 0.26 (氯仿：甲醇=9 ·· 1); NMR (DMSO-d^) ：δ 12.77 (1Η, brs), 10.80 (1H, brs), 9.94 (1H, s), 7.93 (2H, d, J=8.8Hz), 7.88 (1 H, d, J=2.2Hz), 7.82 (2H, d, J=8.8Hz), 7.61 (1 H, dd, J=2.2 and 8·8Ηζ), 7.54 (1 H, d, J=8.8Hz)，3.18 (2H, 似t)，1·66-1.51(2H，m),1·37· 1.19 (2H，m), 0.74 (3H, t, J=7.2Hz)。 本紙張尺度適用中國國家標車（CNS ) Α4規格（210X 297公釐） 236 3933 1 523506 A7 B7 五、發明説明（2 37) 參者例5 1 4-(2-硝基-5-甲基笨硫基甲基）苯甲酸甲酯 .COOMeCOOH TLC: R f 0.26 (chloroform: methanol = 9 ·· 1); NMR (DMSO-d ^): δ 12.77 (1Η, brs), 10.80 (1H, brs), 9.94 (1H, s), 7.93 (2H , d, J = 8.8Hz), 7.88 (1 H, d, J = 2.2Hz), 7.82 (2H, d, J = 8.8Hz), 7.61 (1 H, dd, J = 2.2 and 8 · 8Ηζ), 7.54 (1 H, d, J = 8.8Hz), 3.18 (2H, like t), 1.66-1.51 (2H, m), 1.37 · 1.19 (2H, m), 0.74 (3H, t, J = 7.2Hz). This paper size applies to China National Standard Vehicle (CNS) A4 specification (210X 297 mm) 236 3933 1 523506 A7 B7 V. Description of the invention (2 37) Participant example 5 1 4- (2-nitro-5-methyl Benzothiomethyl) methyl benzoate. COOMe

N〇2 4-乙醯基硫甲基笨甲酸甲酯（794mg)之甲醇（5.0ml)溶 液中，在氩氣及下，依序添加甲醇鈉（191mg)及3-氟-4-硝基甲笨（ 500 ®g),媛慢升至室溫，攪拌4小時，反應混 合物中添加氛化銨飽和水溶液，Μ乙酸乙酯萃取，洗淨、 乾燥並減壓濃縮，殘留物Μ乙醇再结晶，得具下列物理數 據之標鼷化合物（646 mg)。 TLC: Rf 0.49(己烷：二氯甲烷：乙酸乙酯=8:4:1)。 奮_例56 4-[2-(N -異丙基-2 -呋喃磺醸胺基）-5 -甲基笨硫基甲基]甲 酸To a solution of methyl 4-ethylammonium thiomethyl benzoate (794 mg) in methanol (5.0 ml), sodium methoxide (191 mg) and 3-fluoro-4-nitro were sequentially added under argon. Meben (500 g), slowly raise to room temperature, stir for 4 hours, add saturated aqueous ammonium saturated solution, extract with ethyl acetate, wash, dry, and concentrate under reduced pressure. Residue ethanol A standard amidine compound (646 mg) with the following physical data was obtained. TLC: Rf 0.49 (hexane: dichloromethane: ethyl acetate = 8: 4: 1). Fen_Example 56 4- [2- (N -Isopropyl-2 -furansulfonamido) -5 -methylbenzylthiomethyl] formic acid

.COOH.COOH

經濟部中央標準局員工消費合作社印製Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

(請先閲讀背面之注意事項再填寫本頁) 使用4-(2-硝基-5-甲基苯硫基甲基）苯甲酸甲酯（由參 考例51合成），依參考例114參考例24實施例174實施例 2般操作，得具下列物理數據之標題化合物。 T L C : R f 0 . 4 5 (氯仿：甲醇：乙酸=1 0 0 : 5 : 1 ); 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 237 393 3 1 523506 A7 B7 五、發明説明（ 2 38) NMR： 58.04(2H,d,J=8.4Hz), 7.58(lH,dd,J=0-8,1.8Hz) ,7.48(2H,d,J = 8.4Hz), 7·08(1Η,πι), 6·91-6·98(2Η,πι), 6.84(lH,d,J = 8.0Hz), 6.50(lH,dd,J = 2.0,3.8Hz), 4·47 (lH,sept,J=6.8Hz), 4.19(2H,s)， 2.28(3H,s), 1·16(3Η ,d,J=6-8Hz), 1.06(3H,d,J=6.8Hz) g 例 57 4 - [2-(M-異丁基- 2-1«吩基磺醸胺基）-5-三氟甲基苯氧甲 基]桂皮酸 經濟部中央標準局員工消費合作社印製 使用2 -硝基-5 -三氟甲基酚，依參考例1 8 ( b ) 參考例 124參考例24實施例17»&gt;實施例2般操作，得具下列物理 數據之標題化合物。 TLC: Rf 0,51(氯仿：甲醇：乙酸=100:5:1); NMR： 57.80(lH,d,J=16.2Hz), 7*57(2H,d,J=8.0Hz), 7·22-7·46(6Η,β), 7·16(1Η,ιη), 6e93(lH,dd,J = 4.0,5*2 Hz), 6.49(lH,d,J=16.2Hz), 4*94(2H,brs), 3.45(2H,d, J=7*2Hz), 1.62(lH，m), 0,91(6H,d,J=6.6Hz) 奮）fe例58 6-[2-(N-異丙基-苯磺醢胺基）-5-三氟甲基苯氧甲基）-2-萘甲酸 (請先閱讀背面之注意事項再填寫本頁)(Please read the precautions on the back before filling this page) Use 4- (2-nitro-5-methylphenylthiomethyl) benzoate (synthesized from Reference Example 51) according to Reference Example 114 24 Example 174 Example 2 was followed to obtain the title compound with the following physical data. TLC: R f 0. 4 5 (chloroform: methanol: acetic acid = 1 0 0: 5: 1); this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 mm) 237 393 3 1 523506 A7 B7 5 Explanation of the invention (2 38) NMR: 58.04 (2H, d, J = 8.4Hz), 7.58 (lH, dd, J = 0-8,1.8Hz), 7.48 (2H, d, J = 8.4Hz), 7 08 (1Η, π), 6.91-6.98 (2Η, π), 6.84 (lH, d, J = 8.0Hz), 6.50 (lH, dd, J = 2.0,3.8Hz), 4.47 (lH, sept, J = 6.8Hz), 4.19 (2H, s), 2.28 (3H, s), 1.16 (3Η, d, J = 6-8Hz), 1.06 (3H, d, J = 6.8Hz ) g Example 57 4-[2- (M-isobutyl-2-1 «phenysulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Using 2-nitro-5 -trifluoromethylphenol, following the procedure of Reference Example 18 (b) Reference Example 124 Reference Example 24 Example 17 »&gt; Example 2, the title compound having the following physical data was obtained. TLC: Rf 0,51 (chloroform: methanol: acetic acid = 100: 5: 1); NMR: 57.80 (lH, d, J = 16.2Hz), 7 * 57 (2H, d, J = 8.0Hz), 7 · 22-7 · 46 (6Η, β), 7.16 (1Η, ιη), 6e93 (lH, dd, J = 4.0,5 * 2 Hz), 6.49 (lH, d, J = 16.2Hz), 4 * 94 (2H, brs), 3.45 (2H, d, J = 7 * 2Hz), 1.62 (lH, m), 0,91 (6H, d, J = 6.6Hz) Fen) Example 58 6- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl) -2-naphthoic acid (Please read the precautions on the back before filling this page)

本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 238 39 33 1 523506 A7 B7 五、發明説明（ 239)This paper size applies to Chinese National Standard (CNS) A4 (210X 297 mm) 238 39 33 1 523506 A7 B7 V. Description of the invention (239)

02S02S

使用2-(N-異丙基-苯磺醸胺基）-5-三氟甲基酚（由參 考例24合成）及6-羥甲基-2-萘甲酸乙酯，依參考例18(b) 實施例2般操作，得具下列物理數據之標題化合物。 TLC: Rf 0.55(氯仿：甲醇：乙酸=100:5:1); NHR： 58-74(lH,s), 8.17(lH,dd,J=1.8,8-8Hz), 8.03( lH,d,J=8.4Hz), 8.03(lH,brs), 7.95(lH,d,J=8.8Hz), 7·79-7·87(2Η，βι), 7.61(lH,dd,J = 1.4,8.4Hz), 7·43(1Η, m), 7·32(3Η,ηι), 7·26(2Η,ιη), 5.26(2H，s), 4·39(1Η,πι) ,l-08(3H,d,J=6.6Hz), 1.06(3H,d,J=6.6Hz) g Μ m 59(1)-59(3) 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 使用2-硝基-5-三氟甲基酚，依參考例18(b)4參考例 124實施例274實施例11-&gt;實施例2般操作，得具下列物 理數據之標題化合物。 啻淪例5 9 ( 1 ) 4 - [2-(N-異丙基-2-呋喃醸胺基）-5-三氟甲基笨氧甲基]桂 皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 239 39 3 3 1 523506 Μ Β7 五、發明説明（240)Use 2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenol (synthesized from Reference Example 24) and ethyl 6-hydroxymethyl-2-naphthoate according to Reference Example 18 ( b) Following the procedure of Example 2, the title compound having the following physical data was obtained. TLC: Rf 0.55 (chloroform: methanol: acetic acid = 100: 5: 1); NHR: 58-74 (lH, s), 8.17 (lH, dd, J = 1.8,8-8Hz), 8.03 (lH, d, J = 8.4Hz), 8.03 (lH, brs), 7.95 (lH, d, J = 8.8Hz), 7.79-7 · 87 (2Η, βι), 7.61 (lH, dd, J = 1.4,8.4Hz ), 7.43 (1Η, m), 7.32 (3Η, η), 7.26 (2Η, ιη), 5.26 (2H, s), 4.39 (1Η, π), l-08 (3H , d, J = 6.6Hz), 1.06 (3H, d, J = 6.6Hz) g Μ m 59 (1) -59 (3) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back first) (Fill in this page again.) Using 2-nitro-5-trifluoromethylphenol, refer to Reference Example 18 (b) 4, Reference Example 124, Example 274, Example 11-> Example 2, and obtain the following physical data. Title compound. Example 5 9 (1) 4-[2- (N-Isopropyl-2-furanamido) -5-trifluoromethylbenzyloxymethyl] cinnamic acid This paper is in accordance with Chinese National Standards (CNS ) A4 size (210X 297 mm) 239 39 3 3 1 523506 Μ B7 V. Description of invention (240)

T L C ： R f 0.44 (氯仿：甲醇=9 ·· 1) ·， NM R ：δ 7.76 (1H, d, J=16.2Hz), 7.52 (2H, d, J=8.4H2), 7.38 (1 H, d, J=8.4Hz), 7.32 (1 H, d, J=8.4Hz), 7.28-7.20 (3H, m), 7.17 (1 H&gt; s), 6.45 (1 H, d, J=16.2Hz), 6.24-6.19 (1H, m), 6.11-6.00 (1H, br)，5.20-4.80 (3H, m)，i.40-1.00 (6H, m)。 管_例59 (2) 4-[2-(N-異丁基-2-呋喃醢胺基）-5-三氟甲基笨氧甲基]桂 皮酸TLC: R f 0.44 (chloroform: methanol = 9 ·· 1) ·, NM R: δ 7.76 (1H, d, J = 16.2Hz), 7.52 (2H, d, J = 8.4H2), 7.38 (1 H, d, J = 8.4Hz), 7.32 (1 H, d, J = 8.4Hz), 7.28-7.20 (3H, m), 7.17 (1 H &gt; s), 6.45 (1 H, d, J = 16.2Hz) , 6.24-6.19 (1H, m), 6.11-6.00 (1H, br), 5.20-4.80 (3H, m), i.40-1.00 (6H, m). Example 59 (2) 4- [2- (N-Isobutyl-2-furanamido) -5-trifluoromethylbenzyloxymethyl] cinnamic acid

T L C ： R f 0.49 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) NMR ：δ 7.76 (1Η, d, J=15.9Hz), 7.52 (2H, d, J=8.4Hz), 7.39 (1H, d, J=8.1Hz), 7.33-7.15 (5H, m), 6.45 (1H, d, J=15.9Hz), 6.28-6.10 (2H, m), 5.20-4.90 (2H, m), 4.00-3.80 (1H, br), 3.60-3.30 (1H, br), 2.00-1.80 (1H, m), 0.95 (6H, d, J=6.6Hz)。 啻撫例5 9 ( 3 ) 、 4-[2-(N-異丙基-丁醢胺基）-5-三氟甲基苯氧甲基]桂皮酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 240 39 3 3 1 523506 A7 B7 五、發明説明（241)TLC: R f 0.49 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) NMR: δ 7.76 (1Η, d, J = 15.9Hz), 7.52 (2H, d, J = 8.4Hz), 7.39 (1H, d, J = 8.1Hz), 7.33-7.15 (5H, m), 6.45 (1H, d, J = 15.9Hz), 6.28-6.10 (2H, m), 5.20-4.90 (2H, m), 4.00-3.80 (1H, br), 3.60-3.30 (1H, br), 2.00-1.80 (1H, m), 0.95 (6H, d, J = 6.6Hz). Example 5 9 (3), 4- [2- (N-isopropyl-butylammoniumamino) -5-trifluoromethylphenoxymethyl] cinnamic acid This paper applies Chinese national standard (CNS) A4 specifications (210X 297 mm) 240 39 3 3 1 523506 A7 B7 V. Description of the invention (241)

TLC ： R f 0·42 (氯仿··甲醇=9 : 1); NMR ：δ 7.78 (1Η, d, J=15.9Hz), 7.58 (2H, d, J=8.1Hz), 7.42 (2H, d, J=8.1Hz), 7.35-7.20 (3H, m), 6.48 (1H, d, J=15.9Hz), 5.20-4.93 (3H, m), 1.90 (2H, dt, J=2.7, 7.5Hz), 1.64-1.50 (2H, m), 1.17 (3H, d, J=6.6Hz), 0.94 (3H, d, J=6.6Hz), 0.79 (3H, t, J=7.2Hz)〇 啻淪例 60 )-60 (2) 使用2-硝基-5-三氟甲基酚，依參考例18(b)4參考例 124參考例24實施例19·&gt;實施例2般操作，得具下列物理 數據之標題化合物。 窖施例60 (1丄 4-[2-(Ν-異丙基-4-乙氧基苯磺醸胺基）-5-三氟甲基苯氧 甲基]桂皮酸TLC: R f 0 · 42 (chloroform ·· methanol = 9: 1); NMR: δ 7.78 (1Η, d, J = 15.9Hz), 7.58 (2H, d, J = 8.1Hz), 7.42 (2H, d , J = 8.1Hz), 7.35-7.20 (3H, m), 6.48 (1H, d, J = 15.9Hz), 5.20-4.93 (3H, m), 1.90 (2H, dt, J = 2.7, 7.5Hz) , 1.64-1.50 (2H, m), 1.17 (3H, d, J = 6.6Hz), 0.94 (3H, d, J = 6.6Hz), 0.79 (3H, t, J = 7.2Hz). Example 60 ) -60 (2) Using 2-nitro-5-trifluoromethylphenol, following Reference Example 18 (b) 4 Reference Example 124 Reference Example 24 Example 19 &gt; Example 2 The following physical properties were obtained: Data title compound. Cellar Example 60 (1 丄 4- [2- (N-isopropyl-4-ethoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid

02S 經濟部中央標準局員工消費合作社印製 (請先閱讀背面之注意事項再填寫本頁) 〇c2h5 i TLC ： R f 0.51 (氯_ 仿：甲醇=9 : 1) ; ^ NM R ： δ 7.82 (1 H, d, J=16.0Hz), 7.72 (2H, d, J=8.8Hz), 7.61 (2H, d, J=8.6Hz), 7.48 (2H, d, J=8.6Hz), 7.28-7.22 (3H, m), 6.77 (2H, d, J=8.8Hz), 6.50 (1H, d, J=16.0Hz), 5.10 (2H, s), 4.40-4.20 (1H, m), 4.01 (2H, q, J=6.8Hz), 1.43 (3H, t, J=6.8Hz), 1.07 (3H, d, J=6.6Hz), 1.03 (3H, d, J=6.6Hz)〇 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐） 241 39 3 3 1 523506 A7 B7 五、發明説明（ 2 42) n m m R〇 (2) 4 - [2-(N-異丁基-4-乙氧基苯磺釀胺基）-5-三氟甲基苯氧 甲基]桂皮酸02S Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 〇c2h5 i TLC: R f 0.51 (Chlorine_ Imitation: Methanol = 9: 1); ^ NM R: δ 7.82 (1 H, d, J = 16.0Hz), 7.72 (2H, d, J = 8.8Hz), 7.61 (2H, d, J = 8.6Hz), 7.48 (2H, d, J = 8.6Hz), 7.28- 7.22 (3H, m), 6.77 (2H, d, J = 8.8Hz), 6.50 (1H, d, J = 16.0Hz), 5.10 (2H, s), 4.40-4.20 (1H, m), 4.01 (2H , q, J = 6.8Hz), 1.43 (3H, t, J = 6.8Hz), 1.07 (3H, d, J = 6.6Hz), 1.03 (3H, d, J = 6.6Hz) National Standard (CNS) A4 specification (210X297 mm) 241 39 3 3 1 523506 A7 B7 V. Description of the invention (2 42) nmm R〇 (2) 4-[2- (N-isobutyl-4-ethoxy Benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid

(請先閱讀背面之注意事項再填寫本頁)(Please read the notes on the back before filling this page)

COOH NMR ： 5 7.81 (1H, d, J=15.6Hz), 7.60-7.47 (3H, m), 7.44 (1H, d, J=8.2Hz), 7.30-7.10 (5H, m), 6.73(2H, d, J=8.8Hz), 6.50 (1 H, d, J=15.6Hz), 5.00-4.80 (2H, br), 3.95 (2H, q, J=7.0Hz), 3.39 (2H, d, J=6.8Hz), 1.70-1.50 (1 H, m), 1.41 (3H, t, J=6.8Hz), 0·88 (6H，d, J=6.6Hz)。 管_例fil 4-[ 2 -(N-異丙基-3-乙氧基苯磺醯胺基）-5-三氟甲基苯氧 甲基]笨甲酸COOH NMR: 5 7.81 (1H, d, J = 15.6Hz), 7.60-7.47 (3H, m), 7.44 (1H, d, J = 8.2Hz), 7.30-7.10 (5H, m), 6.73 (2H, d, J = 8.8Hz), 6.50 (1 H, d, J = 15.6Hz), 5.00-4.80 (2H, br), 3.95 (2H, q, J = 7.0Hz), 3.39 (2H, d, J = 6.8Hz), 1.70-1.50 (1 H, m), 1.41 (3H, t, J = 6.8Hz), 0 · 88 (6H, d, J = 6.6Hz). Example_fil 4- [2-(N-Isopropyl-3-ethoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzamic acid

COOH 經滴部中央標準局負工消費合作社印製COOH Printed by the Consumer Standards Cooperative of the Central Bureau of Standards

〇2S 〇c2h5 使用4-(2-胺基-5-三氟甲基苯氧甲基）苯甲酸甲酯（由 參考例17合成），依實施例44實施例194實施例2般操作 ,得具下列物理數據之標題化合物。 TLC : Rf 0 · 63 (氯仿：甲醇=9 : 1 ); 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 242 39 33 1 523506 A7 B7 經濟部中央標準局員工消費合作社印製 五、發明説明（2 43 ) HMR： 58.15(2H,d,J=8.4Hz), 7-53(2H,d,J=8.4Hz), 7·40-7·20(6Η，πι), 7.02(lH,ddd,J = 1.2,2.4,8.0Hz), 5.13(2H,s), 4-52-4.36(1H,m), 3.98(2H,q,J = 6*8Hz), 1.40(3H,t,J=6.8Hz), 1.08(3H,d,J=6,6Hz)， 1.06(3H，d, J=6·6Hz) 管淪例 62(1)-62 (2) 使用2-硝基笨甲醸氯，依實施例114參考例2〇~&gt;參考 例24實施例2般操作，得具下列物理數據之標題化合物。 管）fe 例 62 (1 ) 4-[2-(3-氯苯磺醸胺基）苯甲醸胺基]苯甲酸〇2S 〇c2h5 Using 4- (2-amino-5-trifluoromethylphenoxymethyl) benzoic acid methyl ester (synthesized from Reference Example 17), the same operation as in Example 44 Example 194 Example 2 was obtained, The title compound with the following physical data. TLC: Rf 0 · 63 (chloroform: methanol = 9: 1); this paper size applies to China National Standard (CNS) A4 (210X 297 mm) 242 39 33 1 523506 A7 B7 Fifth, the description of the invention (2 43) HMR: 58.15 (2H, d, J = 8.4Hz), 7-53 (2H, d, J = 8.4Hz), 7 · 40-7 · 20 (6Η, π), 7.02 (lH, ddd, J = 1.2,2.4,8.0Hz), 5.13 (2H, s), 4-52-4.36 (1H, m), 3.98 (2H, q, J = 6 * 8Hz), 1.40 (3H , t, J = 6.8Hz), 1.08 (3H, d, J = 6,6Hz), 1.06 (3H, d, J = 6.6Hz) Examples 62 (1) -62 (2) Use of 2-nitrate The methyl benzamidine chloride was operated in the same manner as in Example 114, Reference Example 20 to &gt; Reference Example 24, Example 2 to obtain the title compound having the following physical data. Tube) fe Example 62 (1) 4- [2- (3-chlorobenzenesulfonylamino) benzylamino] benzoic acid

〇2s〇2s

Orcl TLC ： R f 0.38 (氯仿：甲醇=9 : 1) NMR (DMSO-d6) ： 10.59 (1H, s), 10.44 (1H, s), 7.95 (2H, d, J=8.4Hz), 7.86-7.60 (6H, m), 7.58-7.45 (2H, m), 7.38-7.25 (2H, m)〇 管渝俐fi2 (2) 4-[2-(4 -溴苯磺醸胺基）苯甲醯胺基]苯甲酸 本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 243 3933 1 (請先閲讀背面之注意事項再填寫本頁) 公告本 • s，(Orcl TLC: R f 0.38 (chloroform: methanol = 9: 1) NMR (DMSO-d6): 10.59 (1H, s), 10.44 (1H, s), 7.95 (2H, d, J = 8.4Hz), 7.86- 7.60 (6H, m), 7.58-7.45 (2H, m), 7.38-7.25 (2H, m) 〇 Yuli fi2 (2) 4- [2- (4-bromobenzenesulfonylamino) benzamidine Amine] benzoic acid This paper is sized for China National Standard (CNS) A4 (210X 297 mm) 243 3933 1 (Please read the precautions on the back before filling this page) Bulletin • s, (

U 附件 五 申請曰期 yL η、卜 1 案 號 (拿 d 類 别 4^!^ %ς (以上各欄由本局填註） A4 C4 523506 經濟部甘^-^4^;9工&gt;/]骨合作社印製 專利説明書 發明 一、名稱 35ΠΕ 中 文 磺醯胺或脲衍生物及含其作為活性成分之藥劑 英 文 SULFONAMIDE OR CARBAMIDE DERIVATIVES AND DRUGS CONTAINING THE SAME AS ACTIVE INGREDIENTS 姓 名 1.大內田修一1 2.長尾悠樹 國 籍 日本國 一 發明， -Λ m於人 •mw 住、居所 1 2.日本國大阪府三島郡島本町桜井3 丁目1番1號 小野藥品工業股份有限公司水無瀨總合研究所内 姓 名 小野藥品工業股份有限公司 (名稱） 國 籍 日本國 三、申請人 住、居所 (事務所） 曰本國大阪市中央區道修町2丁目1番5號 代表人 姓 名 上野利雄 本紙張尺度適用中國國家標準（cns)a4規格（2iox 297公釐）1 (修正頁）39331 523506 附件三 經濟部智慧財產局員工消費合作社印製U Annex V Application date yL η, Bu 1 case number (take d category 4 ^! ^% Σ (the above columns are filled by this Office) A4 C4 523506 Ministry of Economic Affairs ^-^ 4 ^; 9 工 &gt; // ] Bone Cooperative Co., Ltd. Printed Patent Specification Invention I. Name 35Π Chinese Sulfamidamide or Urea Derivatives and Medicaments Containing It as Active Ingredients 2. Nagao Yuki Nationality was invented in Japan, -Λ m 于 人 • mw Residence, domicile 1 2. Research in Mizuno 3, Choshima, Mishima-gun, Osaka Prefecture, Japan Name of the office Ono Pharmaceutical Industry Co., Ltd. (Name) Nationality Japan III. Applicant's residence, domicile (office) Name of the country No. 2 No. 1, No. 5, Dosho-cho, Chuo-ku, Osaka, Japan Representative name Ryo Ueno This paper is for Chinese countries Standard (cns) a4 specifications (2iox 297 mm) 1 (revised page) 39331 523506 Annex III Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

PGE2之激動劑，所謂PGE2本身多數為已知，但拮抗 PGE2而抑制PGE2作用之化合物（拮抗劑）則大多為未知。 例如，PGE2之拮抗劑揭示+於例如下列之專利申請案。 W0 96/03380中揭示Μ通式（A)所示之化合物為PGE拮 抗劑：The agonist of PGE2, so-called PGE2 itself is mostly known, but the compounds (antagonists) that antagonize PGE2 and inhibit the action of PGE2 are mostly unknown. For example, PGE2 antagonists are disclosed in, for example, the following patent applications. WO 96/03380 discloses that the compound represented by the general formula (A) is a PGE antagonist:

(式中，Α表示可經取代之苯基等，Β表示可經取代之 環系，D表示可經取代之環系，R1A表示羧基等，R 2 A表-示 氫原子，Ci-6烷基等，R3A表示氫原子，Ci-4烷基， 示氫原子或Cl-4烷基。（摘錄一部份））。 W0 96/06822中揭示以通式（B)所示之化合物為PGE拮 抗劑： R38(In the formula, A represents a phenyl group which may be substituted, etc., B represents a ring system which may be substituted, D represents a ring system which may be substituted, R1A represents a carboxyl group, etc., R 2 A represents a hydrogen atom, and Ci-6 alkane. R3A represents a hydrogen atom, a Ci-4 alkyl group, a hydrogen atom or a Cl-4 alkyl group (excerpt part)). WO 96/06822 discloses that the compound represented by the general formula (B) is a PGE antagonist: R38

(式中，A表示可經取代之環系，B表示可經取代之雜 芳環或可經取代之苯基等，D表示可經取代之環系，XB表示 ((：[1!?48)118或（CHR4B)pCR4B = CR4B(CHR4B)ci，818表示後基等 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 2 (修正1 ) (請先閱讀背面之注意事項再填寫本頁) 523506 ;A7 ..., . 、B7、(In the formula, A represents a substitutable ring system, B represents a substitutable heteroaryl ring or a substitutable phenyl group, etc., D represents a substitutable ring system, and XB represents ((: [1!? 48 ) 118 or (CHR4B) pCR4B = CR4B (CHR4B) ci, 818 indicates that the base paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) 2 (Amendment 1) (Please read the notes on the back first) (Please fill in this page for matters) 523506; A7 ...,., B7,

I \ 五、發明說明（3 ) \ ,R3B表示氫原子或Ci-4烷基，R4B表示氫原子或Ci-4烷基 。（摘錄一部份））。 W0 96/1 1902中揭示通式（C)表示之化合物為PGE拮抗 劑：I \ V. Description of the invention (3) \, R3B represents a hydrogen atom or a Ci-4 alkyl group, and R4B represents a hydrogen atom or a Ci-4 alkyl group. (Excerpt part)). W0 96/1 1902 discloses that the compound represented by the general formula (C) is a PGE antagonist:

1C1C

,z~8/R, z ~ 8 / R

A 、〇/?Η、〇 (C)A, 〇 /? Η, 〇 (C)

RR

3C (式中，A,B及D表示各種環系，R1C表示羧基等，R3G 表示氫原子或Ci-4烷基，Z表示- (CH(R5C))mc等。（摘錄一 部份））。 又另一方面，與本發明化合物结構類似之化合物為已 知。例如 Justus Liebigs Ann· Chem· (1909)， 367, 133中 揭示M下化合物： 經濟部智慧財產局員工消費合作社印製3C (where A, B and D represent various ring systems, R1C represents a carboxyl group, etc., R3G represents a hydrogen atom or Ci-4 alkyl group, Z represents-(CH (R5C)) mc, etc. (excerpt part)) . On the other hand, compounds similar in structure to the compounds of the present invention are known. For example, Justus Liebigs Ann · Chem · (1909), 367, 133 reveals compounds under M: printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs

(D) (式中RD表示氫原子，乙基）。又，Khim· Geterotsikl. Soedin(1974), (6)， 760中揭示Μ下化合物： 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 3 (修正頁） 523506 .A7.， ，.::r， B7 '' 丨:_ ' ’ / ^ \ \ i ' 五、發明說明（9 ) 0 ^ S &gt; HZ6 (式中，Z6表示氫或Cl-4烷基）、 Z 7 - C i - 4伸烷基、 C 1 - 4伸烷基-Z 7、 C 1 - 3伸烷基-Z 7 - C 1 - 3伸烷基、 [式中Z7表示0、S或NR6(式中R6具前述相同意義）]、 NZ6S〇2(式中，Z6具前述相同意義）、 C0 ^ C 0 - C 1 - 4伸烷基、 C 1 - 4伸烷基-C 0、(D) (wherein RD represents a hydrogen atom and ethyl group). Also, Khim · Geterotsikl. Soedin (1974), (6), 760 reveals the following compounds: This paper size applies the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 3 (correction page) 523506 .A7. ,,. :: r, B7 '' 丨: _ '' / ^ \ \ i 'V. Description of the invention (9) 0 ^ S &gt; HZ6 (wherein, Z6 represents hydrogen or Cl-4 alkyl), Z 7-C i-4 alkylene, C 1-4 alkylene-Z 7, C 1-3 alkylene-Z 7-C 1-3 alkylene, [wherein Z7 represents 0, S or NR6 (Where R6 has the same meaning as above)], NZ6S〇2 (wherein Z6 has the same meaning as above), C0 ^ C 0-C 1-4 alkylene, C 1-4 alkylene -C 0,

Ci-3伸烷基-CO-Ci-3伸烷基、 C 2 - 4伸烷基、 C 2 - 4伸烯基、 C 2 - 4伸炔基、 R3表示氫、Cl-6烷基、Ci-6烷氧基、Cl - 6烷硫基、硝 基、鹵素、三氟甲基、三氟甲氧基、羥基或羥甲基， R4表示 (1) 氫， (2) Cl-8燒基，C2-8稀基，C2-8快基， (3) 經1或2個選自C00Z8、CONZ9Z10、0Z8基（各基中、 Z8、Z9、Z1G各分別表示氫或Cl-4烷基）、Ci-4烷氧基 -Ci-4烷氧基之組群之基取代之Cl-6烷基， (4) C3-7環烷基， (5) 經苯基或C3-7環烷基取代之Ci-4烷基、C2-4烯基 或C 2 - 4块基 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） (請先閱讀背面之注意事項再填頁)Ci-3 alkylene-CO-Ci-3 alkylene, C 2 -4 alkylene, C 2 -4 alkylene, C 2 -4 alkylene, R3 represents hydrogen, Cl-6 alkyl, Ci-6 alkoxy, Cl-6 alkylthio, nitro, halogen, trifluoromethyl, trifluoromethoxy, hydroxy or hydroxymethyl, R4 represents (1) hydrogen, (2) Cl-8 Group, C2-8 dilute group, C2-8 fast group, (3) 1 or 2 groups selected from C00Z8, CONZ9Z10, 0Z8 (in each group, Z8, Z9, Z1G each represents hydrogen or Cl-4 alkyl group ), Ci-6 alkoxy-Ci-4 alkoxy group group substituted Cl-6 alkyl, (4) C3-7 cycloalkyl, (5) phenyl or C3-7 cycloalkane Basic substituted Ci-4 alkyl, C2-4 alkenyl or C 2-4 pieces of paper. Applicable to China National Standard (CNS) A4 (210 X 297 mm). (Please read the precautions on the back before filling in the page. )

JR 經濟部智慧財產局員工消費合作社印製 9 (修正頁） 523506 Α7 6〇 C i · 五、發明說明（10) [上述（4)及（5)中之苯基、C3-7環烷基可經in個R5基（ m及R5如前述相同定義）取代], η及t各自分別為1-4之整數； 但是，（1 ) R 2及Z 3各僅鍵结在（0之1位及2位上， (2 ) @表示苯環（Z2)t不表示C0R1時，Z1僅鐽结至苯環Printed by the Employees' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 9 (revised page) 523506 Α7 60C i · V. Description of the invention (10) [Phenyl, C3-7 cycloalkyl in (4) and (5) above May be substituted by in R5 groups (m and R5 have the same definitions as above)], η and t are each an integer of 1-4; however, (1) each of R 2 and Z 3 is only bonded to the 1st position of (0) At the 2nd position, (2) @ represents a benzene ring (Z2) and t does not represent C0R1, Z1 is only bound to a benzene ring

COO-tBu 或 2) 其製造方法，及 3) 含其作為有效成分之PGE2拮抗或激動劑。 通式（I)中，Z5及R4中之Ci-4烷基及Z2, Z6, Z8, Z9, Ζ 基 R6, R7及R8表示之Ci-4烷基，意指甲基、乙基、丙 丁基及其異構體。 意指甲基、乙基 通式（I)中， 基、丙基、丁基 通式（I)中， 經濟部智慧財產局員工消費合作社印製 通式（I)中，R4之Ci-6烷基，R3及R5表示之Ci-6烷基， 丙基、丁基、戊基、己基及其異構體。 Z5及R4表示之Ci-8烷基，意指甲基、乙 戊基、己基、庚基、辛基及其異構體。 Z5及R4中之C2-4烯基，意指乙烯基、丙 鍤基、丁烯基及其異構體。 通式（I)中，Z5及R4表示之C2-8烯基，意指C2-8烷基 中含有1〜3個雙鍵者，例如乙烯基，丙烯基、丁烯基、戊 烯基、己烯基、庚烯基、辛烯基及其異構體。 通式（I)中，Z5及R4中之C2-4炔基，意指乙炔基、丙 炔基、丁炔基及其異構體。 通式（I)中，Ζ5及R4表示之C2-8炔基，意指C2-8烷基 中含1〜3個蓥鍵者，例如乙炔基，丙炔基，丁炔基，戊炔 10 (修正頁） 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 523506 A7 Bt 五、發明說明（20) 化合物： 88· rm 7tr (R3b)n dbCOO-tBu or 2) its manufacturing method, and 3) a PGE2 antagonist or agonist containing it as an active ingredient. In the general formula (I), Ci-4 alkyl groups in Z5 and R4 and Ci-4 alkyl groups represented by Z2, Z6, Z8, Z9, and Z groups R6, R7, and R8 mean methyl, ethyl, and butyl And its isomers. It means that in the general formula (I) of methyl, ethyl, propyl, butyl, and butyl, the general formula (I) of the Intellectual Property Bureau of the Ministry of Economic Affairs, printed by the consumer cooperative of the general formula (I), Ci-6 of R4 Alkyl, Ci-6 alkyl represented by R3 and R5, propyl, butyl, pentyl, hexyl and its isomers. Ci-8 alkyl represented by Z5 and R4 means methyl, ethylpentyl, hexyl, heptyl, octyl and its isomers. C2-4 alkenyl in Z5 and R4 means vinyl, propenyl, butenyl and its isomers. In the general formula (I), C2-8 alkenyl represented by Z5 and R4 means a C2-8 alkyl group containing 1 to 3 double bonds, such as vinyl, propenyl, butenyl, pentenyl, Hexenyl, heptenyl, octenyl and their isomers. In the general formula (I), the C2-4 alkynyl group in Z5 and R4 means ethynyl, propynyl, butynyl and its isomers. In the general formula (I), C2-8 alkynyl represented by Z5 and R4 means a C2-8 alkyl group containing 1 to 3 hydrazone bonds, such as ethynyl, propynyl, butynyl, and pentyne 10 (Revised page) This paper size is in accordance with Chinese National Standard (CNS) A4 (210 X 297 mm) 523506 A7 Bt V. Description of the invention (20) Compound: 88 · rm 7tr (R3b) n db

(lb-2) R (式中 R21 表示式 NR8C0、Ci-4 伸烷基- NR8C0、NR8C〇-Cl-4伸烷基或（^-3伸烷基- NR8C0-Ci-3伸烷基（式中所有符 號具有前述相同定義），其他符號具前逑之相同定義），係 使通式（VI)所示之化合物：(lb-2) R (where R21 represents the formula NR8C0, Ci-4 alkylene-NR8C0, NR8C0-Cl-4 alkylene or (^ -3 alkylene-NR8C0-Ci-3 alkylene ( All symbols in the formula have the same definitions as above, and other symbols have the same definitions as before), which make the compound represented by general formula (VI):

(R3b)n-( B 1 R200-NHRa Ύ-N-Z4- Z5b R4b (VI) (式中，所有符號具有前述相同定義）與通式（VII)所 示之化合物： 請 先 閱 讀 背 面 之 注 意 事 項 再 填』 頁 經濟部智慧財產局員工消費合作社印製 z1b 、(Z2b)t HOOC-R-^TX (V 丨丨) (式中，所有符號具有前述相同定義）， 進行醯胺化反應而製得。 醢胺化反應係K前述（3)所載之相同方法進行。 (7)通式（lb)中，R2為 0、S、NZ6、Z7-Ci-4 伸烷基、 Cl-4伸烷基-Z7或Cl-3伸烷基-Z7-Ci-3伸烷基（式中，所 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 20 (修正頁） 523506 881 |B7^ ^ … 五、發明說明（21 ) 有符號具有前述相同定義）所示之基之通式（Ib-3)所示之 化合物： 7 1b (R3b)(R3b) n- (B 1 R200-NHRa Ύ-N-Z4- Z5b R4b (VI) (where all symbols have the same definitions as above) and compounds represented by general formula (VII): Please read the notes on the back first Re-fill the matter "page printed by z1b, (Z2b) t HOOC-R- ^ TX (V 丨 丨) (Equation, all symbols have the same definition as above), printed by z1b, (Z2b) t HOOC-R- ^ TX (V 丨 丨) Obtained. The amidation reaction is performed in the same manner as described in (3) above. (7) In the general formula (lb), R2 is 0, S, NZ6, Z7-Ci-4 alkylene, Cl-4 Alkyl-Z7 or Cl-3 Alkyl-Z7-Ci-3 Alkyl (wherein the paper size applies the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 20 (correction page) 523506 881 | B7 ^ ^… V. Description of the invention (21) A compound represented by the general formula (Ib-3), which has a base represented by the same definition as above: 7 1b (R3b)

(lb-3) FT 請 先 閱 讀 背 面 之 注 意 事 項 再 填 (式中，R22 表示 0、S、NZ6、Z7-Ci“4伸烷基、Ci-4 伸 烷基_〖7或Ci-3伸烷基伸烷基（式中，所有符號具 有前述相同定義）所示之基，其他符號具有前述相同定義） ，係使用通式（VIII)所示之化合物： 1 R22(lb-3) FT Please read the precautions on the back before filling in (where R22 represents 0, S, NZ6, Z7-Ci "4-alkylene, Ci-4 alkylene_ 〖7 or Ci-3 Alkyl alkylene (wherein all symbols have the same definitions as previously described), and other symbols have the same definitions as above, using compounds represented by general formula (VIII): 1 R22

(R3b)n-( B zib(Z2b)t (Vlil) 4b 經濟部智慧財產局員工消費合作社印製(R3b) n- (B zib (Z2b) t (Vlil) 4b

、z3—NHR (式中，所有符號具有前述相同定義），與通式（IX)所 示之化合物： X-Z4,Z5b (IX) (式中，X表示鹵素，其他符號具有前逑相同定義）， 進行磺醢胺化或醯胺化反應而製得。 磺醯胺化或醯胺化反應係例如在惰性有機溶劑（THF, 二氯甲烷、苯、丙酮、乙腈等）中，在三級胺（二甲胺基吡 啶、吡啶、三乙胺等）存在下或不存在下，在〇〜50¾進行 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 21 (修正頁） 523506 A7 B7 五、發明說明（40) 6463-6466(1992)]調製類前列腺素受體亞型（小鼠EP1)表 現之 CH0细胞作為膜標本。 所調製之膜畫分（O.Smg/ml)與含3H-PGE2之反應液（ 2 0 0 /i 1 )在室溫下於恒溫箱中置1小時。Μ冰冷之鑀衝液（ 3ml)停止反應，經玻璃過滤器（GF/B)減壓抽吸過漶經结合 之3H-PGE2於阱中，Μ液體內爍器測定结合放射活性。 以Scatchard作圖求取Kd值及Bmax值[Ann· Ν·Υ·, Z3—NHR (where all symbols have the same definitions as above), and compounds represented by general formula (IX): X-Z4, Z5b (IX) (where X is halogen, other symbols have the same definition as before ), Prepared by sulfonamidation or amidation reaction. Sulfonation or sulfonation reactions occur, for example, in inert organic solvents (THF, dichloromethane, benzene, acetone, acetonitrile, etc.), and tertiary amines (dimethylamine pyridine, pyridine, triethylamine, etc.) In the absence or absence, the paper size shall be in the range of 0 ~ 50¾. Applicable to the Chinese National Standard (CNS) A4 (210 X 297 mm) 21 (revised page) 523506 A7 B7 V. Description of the invention (40) 6463-6466 (1992 )] CH0 cells that modulate the expression of prostaglandin receptor subtype (mouse EP1) were used as membrane samples. The prepared film (O.Smg / ml) and the reaction solution (2 0 / i 1) containing 3H-PGE2 were placed in a thermostat at room temperature for 1 hour. The ice-cold solution (3ml) of Μ was used to stop the reaction, and the combined 3H-PGE2 was sucked through the glass filter (GF / B) under reduced pressure. Calculate Kd value and Bmax value using Scatchard chart [Ann · Ν · Υ ·

Acad. Sci· 51, 660(1949)]。非特異结合係在過量（2· 5 /i Μ)非標記PGE 2存在下结合而求得。測定本發明化合物之 3H-PGE2结合抑制作用，係對2.5nM 3H-PGE2添加各種濃度 之本發明化合物而進行者。又，反應中使用下列緩衝液。 媛衝液：10mM 磷酸鉀（pH 6.0), linM EDTA, ΙΟπιΜ MgCl2, 0 . 1M NaC 1 〇 各化合物之解離常數Ki(/i M)M下式求得。 Κι = ICs〇/ (1+ ( [C]/Kd)) 請 先 閱 讀 背 面 之 注 意 事 項 再 填 寫 頁 經濟部智慧財產局員工消費合作社印製 40 (修正頁） 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 523506Acad. Sci. 51, 660 (1949)]. The non-specific binding system was obtained by binding in the presence of an excess (2.5 / iM) of unlabeled PGE2. The 3H-PGE2 binding inhibitory effect of the compound of the present invention was measured by adding various concentrations of the compound of the present invention to 2.5nM 3H-PGE2. The following buffers were used in the reaction. Yuan Yuan solution: 10 mM potassium phosphate (pH 6.0), linM EDTA, 10 μm MgCl2, 0.1 M NaC 1 0 The dissociation constants Ki (/ i M) M of each compound can be obtained by the following formula. Κι = ICs〇 / (1+ ([C] / Kd)) Please read the notes on the back before filling in the page Printed by the Consumers' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 40 (revised page) This paper size applies to Chinese national standards (CNS ) A4 size (210 X 297 mm) 523506

88 8. 2 788 8. 2 7

XI C! 五、發明說明（45) 5-氯胺基苯甲酸甲酯 COOMe NH2 於含5-氯-2-胺基苯甲酸（6.1g)之乙酸乙酯·甲醇（ 20ml+10ml)懸浮液中，在Ot!下加入過量之重氮甲烷之乙 醚（50ml)溶液。反應结束後，反應液減壓濃縮，得列具下 列物理數據之標題化合物（6 . 6 g )。 NMR： 57.82(lH,d), 7*21(lH,dd), 6.60(lH,d), 5.73( 2H,brs), 3.88(3H,s) 參者例2 2-苯磺醯胺基-5-氯苯甲酸甲酯 請 先 閱 讀 背 之 注 意 事 項 再 填 寫 本 頁 C! II 〇2 π 經濟部智慧財產局員工消費合作社印製 5-氯胺基苯甲酸甲酯（由參考例1合成，400rag)及 吡啶（0.87ml)之二氯甲烷溶液在下，添加苯磺醯氯（ 0.33ml),於室溫攪拌隔夜。反應混合物中加入稀塩酸， 以乙酸乙酯萃取。有機層予以洗淨、乾燥及減壓濃縮。殘 留物Μ矽膠管柱層析法（己烷-乙酸乙酯）純化，得到具下 列物理數據之標題化合物（6 6 4 m g )。 TLCL: Rf 0.30(己烷··乙酸乙酯= 4:1); NMR： 5 10.5(1H&gt;S), 7.90-7·79(3Η,πι), 7.79(lH,d), 45 (修正頁） 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 523506 A7 ·-、/ Λ 五、發明說明（17$ ΗΟ.XI C! V. Description of the invention (45) A suspension of methyl 5-chloroaminobenzoate COOMe NH2 in ethyl acetate · methanol (20ml + 10ml) containing 5-chloro-2-aminobenzoic acid (6.1g) In Ot !, an excess of a solution of diazomethane in ether (50 ml) was added. After completion of the reaction, the reaction solution was concentrated under reduced pressure to obtain the title compound (6.6 g) having the following physical data. NMR: 57.82 (lH, d), 7 * 21 (lH, dd), 6.60 (lH, d), 5.73 (2H, brs), 3.88 (3H, s) See Example 2 2-benzenesulfonamido- Methyl 5-chlorobenzoate Please read the precautions before filling in this page C! II 〇 2 π Methyl 5-chloroaminobenzoate (synthesized from Reference Example 1, printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs, 400rag) and pyridine (0.87ml) in a methylene chloride solution, benzenesulfonyl chloride (0.33ml) was added, and the mixture was stirred at room temperature overnight. Dilute osmic acid was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure. The residue M was purified by silica gel column chromatography (hexane-ethyl acetate) to give the title compound (646 mg) having the following physical data. TLCL: Rf 0.30 (hexane · ethyl acetate = 4: 1); NMR: 5 10.5 (1H &S; S), 7.90-7 · 79 (3Η, π), 7.79 (lH, d), 45 (correction page ） This paper size applies to China National Standard (CNS) A4 specification (210 X 297 mm) 523506 A7 ·-, / Λ 5. Description of invention (17 $ ΗΟ.

COOMe 4-(2-甲氧羰乙基）苯甲酸甲酯（1*〇8)之1^卜1^011混 合溶液（12ml; THF: MeOH= 5:1)中，在室溫下添加硼氫化 納（85ing)並攪拌19小時，反應混合物中添加氯化銨，分解 過量試藥後，Μ乙酸乙酯萃取，有機曆洗淨、乾燥並減壓 濃縮，殘留物Κ矽膠管柱層析法（乙酸乙酷：己烷=2:3) 純化，得具下列物理數據之〇Η體（6 9 2 mg)。 TLC: Rf0.38(己烷··乙酸乙酯=I:1)。 (b )目的物COOMe 4- (2-methoxycarbonylethyl) benzoic acid methyl ester (1 * 〇8) in 1 ^ bu 1 ^ 011 mixed solution (12ml; THF: MeOH = 5: 1), boron was added at room temperature Sodium hydride (85ing) and stirring for 19 hours. Ammonium chloride was added to the reaction mixture. After decomposing the excess reagent, it was extracted with ethyl acetate, washed with organic calendar, dried and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography. (Ethyl acetate: hexane = 2: 3) Purified to obtain 〇Η 体 (629) with the following physical data. TLC: Rf 0.38 (hexane · ethyl acetate = 1: 1). (b) the object

COOMe 請 先 閱 讀 背 面 之 注 意 事 項 再 填 經濟部智慧財產局員工消費合作社印製 2-硝基-5-氯酚（150mg)之THF(2.0ml)溶液中，在氬氣 流下，添加上述（a)合成之0H體（168mg)及三苯膦（227mg) 後，在0¾下滴加DEAD(136p1)°反應混合物在室溫攪拌24 小時後，K冰水處理，Μ乙酸乙酯萃取。有機層洗淨、乾 燥並減壓濃縮。殘留物Μ矽膠管柱層析法（己烷：乙酸乙 酯=10 :145:1)純化，得具下列物理數據之標題化合物（ 3 0 9 m g ) 0 TLC: Rf0.24(己烷：乙酸乙酯=5:1)。 g _ 例 22 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 175 (修正頁） 523506 A7 B7； ϋ 五、發明說明（178)COOMe Please read the notes on the back before filling the 2-nitro-5-chlorophenol (150mg) printed in THF (2.0ml) printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs, and add the above (a ) After synthesizing the 0H form (168 mg) and triphenylphosphine (227 mg), DEAD (136p1) ° reaction mixture was added dropwise at 0¾, and the mixture was stirred at room temperature for 24 hours, treated with K ice water, and extracted with ethyl acetate. The organic layer was washed, dried and concentrated under reduced pressure. The residue M was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 145: 1) to obtain the title compound (309 mg) having the following physical data. 0 TLC: Rf0.24 (hexane: acetic acid Ethyl ester = 5: 1). g _ Example 22 This paper size is in accordance with Chinese National Standard (CNS) A4 (210 X 297 mm) 175 (correction page) 523506 A7 B7; ϋ V. Description of the invention (178)

COOHCOOH

CICI

NH 02S T L C : R f 0.40 (氯仿：甲醇：乙酸=100:10:1); NM R (DMSO-d&amp;) ：δ 9.90 (1H, brs), 9.02 (1 H, d, J=1.6Hz), 8.27 (1 H, dd, J=2.2, 8.4Hz), 7.62 (2H, m), 7.49 (2Hf m), 7.31-7.39 (2H, m), 7.31 (1H, d, J-8.6Hz)f 7.08 (1H, d, J=2.2Hz), 7.02 (1H, dd, J=2.2, 8.6Hz), 4.96 (2H, s)〇 宵_湖22 ( 4 ) 4-[；lRS-(2-苯磺醯胺-5-氯苯氧基）乙基]苯甲酸]NH 02S TLC: R f 0.40 (chloroform: methanol: acetic acid = 100: 10: 1); NM R (DMSO-d &amp;): δ 9.90 (1H, brs), 9.02 (1 H, d, J = 1.6Hz) , 8.27 (1 H, dd, J = 2.2, 8.4Hz), 7.62 (2H, m), 7.49 (2Hf m), 7.31-7.39 (2H, m), 7.31 (1H, d, J-8.6Hz) f 7.08 (1H, d, J = 2.2Hz), 7.02 (1H, dd, J = 2.2, 8.6Hz), 4.96 (2H, s) 〇night_Lake 22 (4) 4-[; lRS- (2-benzene Sulfonamide-5-chlorophenoxy) ethyl] benzoic acid]

COOH 請 先 閱 讀 背 面 之 注 意 事 項 再 填 頁 經濟部智慧財產局員工消費合作社印製 T L C ： R t 0.48 (氛仿：甲醇= 9:1); NM R ： δ 12.0-10.0 (1 H, br), 8.00 (2Hf d, J=8.4Hz), 7.78 (2H, d, J=7.8Hz), 7.7- 7.4 (4Hi m), 7·1·7.0 (3H, m), 6.88 (1H，dd.J=2.2· 8.8Hz). 6.45 (1H，s), 5.U (1H q, J=6.4Hz)· 1.50 (3H· d，J =6.4Hz)。 鈇老例1 9 2-硝基-5-三氟甲基苯基甲氧甲基酸 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 178 (修正頁） 523506COOH Please read the notes on the back before filling in the pages printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs: R t 0.48 (Analog: methanol = 9: 1); NM R: δ 12.0-10.0 (1 H, br) , 8.00 (2Hf d, J = 8.4Hz), 7.78 (2H, d, J = 7.8Hz), 7.7- 7.4 (4Hi m), 7.1 · 7.0 (3H, m), 6.88 (1H, dd.J = 2.2 · 8.8Hz). 6.45 (1H, s), 5.U (1H q, J = 6.4Hz) · 1.50 (3H · d, J = 6.4Hz).鈇 Old example 1 9 2-Nitro-5-trifluoromethylphenylmethoxymethyl acid This paper size is in accordance with Chinese National Standard (CNS) A4 (210 X 297 mm) 178 (correction page) 523506

五、發明説明（2〇4) 4-(2-環戊基亞磺醯胺基-5-三氟甲基苯氧甲基）苯甲酸甲酷 COOMeV. Description of the invention (204) 4- (2-Cyclopentylsulfenamido-5-trifluoromethylphenoxymethyl) benzoate COOMe

經濟部智慧財產局員工消費合作社印製 4-(2-胺基-5-三氟甲基苯氧甲基）苯甲酸甲酯（300mg) 之二氯甲烷（3.0ml)溶液中，在氩氣流下添加吡啶（187以1 )及三苯膦（315mg)，在下滴加環戊基磺醯氯（202mg)溶 液，室溫下攪拌6小時。反應混合物中加水，以乙酸乙酯 萃取、洗淨、乾燥及減壓濃縮。殘留物以矽膠管柱層析法 (己烷··乙酸乙酯=2 : 1 1 : 1 )純化，得具下列物理數據之標 題化合物（309mg)。 TLC: Rf 0.23(己烷：乙酸乙酯=2:1)。 啻觖例3ft 4-(2-環戊基磺醯胺基-5-三氟甲基苯氧甲基）苯甲酸甲酯 XOOMer r f3c、Printed by the Consumer Cooperative of Intellectual Property Bureau of the Ministry of Economic Affairs, 4- (2-Amino-5-trifluoromethylphenoxymethyl) benzoic acid methyl ester (300mg) in dichloromethane (3.0ml) solution under argon flow Pyridine (187 to 1) and triphenylphosphine (315 mg) were added thereto, and a solution of cyclopentylsulfonium chloride (202 mg) was added dropwise thereto, followed by stirring at room temperature for 6 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane ·· ethyl acetate = 2: 1 1: 1) to obtain the title compound (309 mg) having the following physical data. TLC: Rf 0.23 (hexane: ethyl acetate = 2: 1). Example 3ft 4- (2-Cyclopentylsulfonamido-5-trifluoromethylphenoxymethyl) benzoate XOOMer r f3c,

MH o2s 4-(2-環戊基磺醯胺基-5-三氟甲基苯氧甲基）苯甲酸 甲酯（305nig;由參考例33合成）之二氯甲综（4.0ml)溶液中 ，在0Ό下添加間-氯過苯甲酸（456mg)，搅拌1小時。反應 (請先閱讀背面之注意事項再填寫本頁)MH o2s methyl 4- (2-cyclopentylsulfonamido-5-trifluoromethylphenoxymethyl) benzoate (305nig; synthesized from Reference Example 33) in dichloromethane (4.0ml) solution Then, m-chloroperbenzoic acid (456 mg) was added at 0 ° C, and the mixture was stirred for 1 hour. Response (Please read the notes on the back before filling this page)

、1T Φ 本紙張尺度適用中國國家標準（CNS ) Α4規格（210X 297公釐） 2 0 4 (修正頁）3 9 3 3 1 523506 B,r 本 五、發明說明（ 2 44) eaJs. 27、 1T Φ The size of this paper applies to Chinese National Standard (CNS) A4 specification (210X 297 mm) 2 0 4 (corrected page) 3 9 3 3 1 523506 B, r Note 5. Invention description (2 44) eaJs. 27

COOH T L C ： R f 0.39 (氯仿：甲醇=9:1); NMR (DMSO-d/) ： 10.55 (1H, s), 10.38 (1H, s), 7.96 (2H, d, J=8.8Hz), 7.90-7.45 (8H, m), 7.44-7.25 (2H, m)〇 製割例1 以下各成分依尋常方法充分混合後，予以打錠，得錠 劑100錠，每錠含5mg之活性成分。 • 4-(2-苯磺醯胺基-5-氯苯甲醢胺基）苯 甲酸（由實施例2合成） 纖維素二醇酸鉀（崩解劑 硬脂酸鎂（潤滑劑） 微晶纖維素 5 0 0 m g 2 0 0 πι g 1 0 0 m g 9 . 2g -----------* (請先閱讀背面之注意事項再填寫本頁) 訂---------線 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐） 2 44 (修正頁）COOH TLC: R f 0.39 (chloroform: methanol = 9: 1); NMR (DMSO-d /): 10.55 (1H, s), 10.38 (1H, s), 7.96 (2H, d, J = 8.8Hz), 7.90-7.45 (8H, m), 7.44-7.25 (2H, m). Cutting example 1 After the following ingredients are thoroughly mixed according to the ordinary method, they are tableted to obtain 100 tablets, each tablet containing 5mg of active ingredient. • 4- (2-benzenesulfonamido-5-chlorobenzylamido) benzoic acid (synthesized from Example 2) potassium cellulose glycolate (disintegrant magnesium stearate (lubricant) microcrystal Cellulose 5 0 0 mg 2 0 0 μm 1 0 0 mg 9. 2g ----------- * (Please read the precautions on the back before filling this page) Order ------ --- Printed by the Consumers' Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs. The paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) 2 44 (correction page)

Claims (1)

H3 公告表 第861 18583號專利申請氧 申請專利範圍修正本 ¾沖 (91年1月25日） 1. 一種通式（I)所示之磺醯胺或脲衍生物及其醫藥可接受 性塩： (R3)rH BH3 Bulletin Form No. 861 18583 Patent Application Oxygen Application Patent Range Amendment (January 25, 91) 1. A sulfonamide or urea derivative represented by general formula (I) and its medical acceptability 塩: (R3) rH B (I) (式中， Θ 爲苯基、萘基、環己基、呋喃基、噻吩 基或吡啶基 ，® 爲苯基、茚滿基、萘基或吡啶基， 經濟部中央標準局員工福利委員會印製 Z1表示下列之基： -COR1 &gt;· CHyCOR1、 -CH^CH^COR1、 -CH=CH-COR1 ^ -C^C-COR1、 -O-CH^COR1 (各式中，R1爲羥基或烷氧基）； 或表示式-CH2-OH之基， Z2表示氫、甲基、甲氧基、羥基或式COR1之基（式中R1 同前述定義）， Z3表示單鍵或伸甲基， Z4表示302或(：〇， 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 1 39331 523506 _H3 Z5表示 (DC^烷基、C2_6烯基， (2) 苯基，C5_6環烷基或噻吩基， (3) 經苯基或C5.6環烷基取代之Cw烷基或C2.4烯基， (4) 經m個（m表示1至3之整數）R5基（其中，各R5分別示 烷基、Cw烷氧基、（^.6烷硫基、硝基、鹵素、三 氟甲基或羥基）所取代之苯基或 (5) 可經1個甲基取代之呋喃基或噻唑基， R2表示下列之基： CONH、 NHCO、 C〇NH-CHr、 〇、 ζ7-ίν3伸烷基、 [式中Ζ7表示0、S或ΝΖ6(式中Ζ6爲氫或甲基)]、 CH2〇、 NHS〇2、 -CH2CH2-、 -CH 二 CH-或、 經濟部中央標準局員工福利委員會印製 -CeC-、 R3表示氫、烷基、甲氧基、硝基、鹵素、三氟甲基 或羥甲基， R4表示 ⑴氫， 院基，C2.8嫌基， (3)經1或2個選自C〇〇Z8、C〇NZ9Z1G、OZ8基（各基中Z8 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 2 39331 523506 _._H3_ 、z9、z1()各分別表示氫或甲基）、甲氧乙氧基所成組群 之基取代之CV4烷基， (4) 環戊基， (5) 經苯基或C3_6環烷基取代之甲基， η爲1或2之整數， t爲1之整數； 之1位及2位上， 但是，（1)R2及Z3各僅鍵結在 (2) 表示苯環，且（Z2)t不表示COR1時，Z1僅鍵 ,Z1 結至苯環之3或4位置，爲(I) (where Θ is phenyl, naphthyl, cyclohexyl, furyl, thienyl or pyridyl, ® is phenyl, indanyl, naphthyl or pyridyl, Staff Welfare Committee of Central Bureau of Standards, Ministry of Economic Affairs The printed Z1 represents the following bases: -COR1 &gt; · CHyCOR1, -CH ^ CH ^ COR1, -CH = CH-COR1 ^ -C ^ C-COR1, -O-CH ^ COR1 (In each formula, R1 is a hydroxyl group Or alkoxy group); or a group of formula -CH2-OH, Z2 represents hydrogen, methyl, methoxy, hydroxyl or a group of formula COR1 (where R1 has the same definition as above), Z3 represents a single bond or a methyl group Z4 means 302 or (: 〇, this paper size applies Chinese National Standard (CNS) A4 specifications (210 X 297 mm) 1 39331 523506 _H3 Z5 means (DC ^ alkyl, C2_6 alkenyl, (2) phenyl, C5_6 cycloalkyl or thienyl, (3) Cw alkyl or C2.4 alkenyl substituted with phenyl or C5.6 cycloalkyl, (4) m through m (m represents an integer from 1 to 3) R5 (Wherein each R5 represents an alkyl group, a Cw alkoxy group, (^ .6 alkylthio, nitro, halogen, trifluoromethyl or hydroxy group) substituted phenyl groups or (5) may be substituted by 1 methyl group Substituted furyl or thiazole R2 represents the following radicals: CONH, NHCO, COH-CHr, 〇, ζ7-ίν3 alkyl, [wherein Z7 represents 0, S or NZ6 (wherein Z6 is hydrogen or methyl)], CH2 〇, NHS〇2, -CH2CH2-, -CH di-CH- or, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs -CeC-, R3 represents hydrogen, alkyl, methoxy, nitro, halogen, trifluoromethyl Group or hydroxymethyl group, R4 represents fluorene hydrogen, academic group, C2.8 group, (3) 1 or 2 groups selected from C00Z8, CNZ9Z1G, OZ8 (Z8 in each base applies to this paper size) Chinese National Standard (CNS) A4 specification (210 X 297 mm) 2 39331 523506 _._ H3_, z9, z1 () each represent hydrogen or methyl), and CV4 substituted by the group formed by methoxyethoxy Alkyl, (4) cyclopentyl, (5) methyl substituted with phenyl or C3-6 cycloalkyl, η is an integer of 1 or 2, and t is an integer of 1; at the 1 and 2 positions, however, (1) Each of R2 and Z3 is bonded only at (2) represents a benzene ring, and (Z2) t does not represent COR1, Z1 is only bonded, and Z1 is bonded to the 3 or 4 position of the benzene ring as COOHCOOH , 之化合物除外）。 經濟部中央標準局員工福利委員會印製 Θ 可接受性塩，其中（a) 2. 如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 可接受性塩，其中 @鮮*'㈣賴Ξ*’ (3 表示苯基、茚滿基、萘基，Z5爲（DCu烷基、C2.6烯基、 (2)苯基或C5.6環烷基、（3)經苯基或C5_6環烷基取代之Cw 烷基或C2.4烯基或⑷經m個(m=l至3)R5基取代之苯基。 3. 如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 示呋喃基、噻吩基或吡啶基 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 3 39331 523506 H3 或（b) (3 示吡啶基，或（c)Z5爲（1)噻吩基或（2)可經1個 甲基取代之呋喃基或噻唑基。 4.如申請專利範圍第1或3項之磺醯胺或脲衍生物及其 醫 藥可接受性塩，其中@爲苯基、萘基或環己基， (3 表示苯基、茚滿基或萘基，Z5爲（1)噻吩基或（2)可 經1個甲基取代之呋喃基或噻唑基。 5.如申請專利範圍第1或3項之磺醯胺或脲衍生物及其 之任一基表示雜 醫藥可接受性塩，其中 環，另一基爲碳環。 6. 如申請專利範圍第1、2或3項之磺醯胺或脲衍生物及其 醫藥可接受性塩，其中R2爲下式所示之基： CONH、 CONH-CHr 或 NHCO。 經濟部中央標準局員工福利委員會印製 7. 如申請專利範圍第1、2或3項之磺醯胺或脲衍生物及 其醫藥可接受性塩，其中R2爲下式所示之基： 〇、 Ζ7-〇ν3伸烷基（式中Z7表示0、S或ΝΖδ(其中Z6爲 氫或甲基））。 8. 如申請專利範圍第1、2或3項之磺醯胺或脲衍生物及 其醫藥可接受性塩，其中R2爲-CH2CHr、-CH=CH-或 -C 三 C-。 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 4 39331 523506 _H3 9.如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 可接受性塩，其係 (1) 4-(2-苯磺醯胺基-5-氯茏甲醯胺基）苯甲酸， (2) 3-(2-苯磺醯胺基苯甲醯胺基）苯甲酸， (3) 3-(2-苯磺醯胺基-5-氯苯甲醯胺基）苯甲酸， (4) 4-(2-苯磺醯胺基苯甲醯胺基）苯甲酸， (5) 4-[2-(4-氯苯基）磺醯胺基-5-氯苯甲醯胺基] 苯甲酸， (6) 4-[2-(4-氯苯基磺醯胺基）-4-氯苯甲醯胺基] 苯甲酸， (7) 4_[2-(4-氯苯基磺醯胺基)-6-氯苯甲醯胺基] 苯甲酸， (8) 4-[2-(4-氯苯基磺醯胺基）-3-氯苯甲醯胺基] 苯甲酸， (9) 4-[2-(2-氯苯基磺醯胺基）-5-氯苯甲醯胺基] 苯甲酸， (10) 4-[2-(3-氯苯基磺醯胺基）-5-氯苯甲醯胺基] 苯甲酸， (11) 4-[2-(4-氯苯基磺醯胺基）-5-氟苯甲醯胺基] 經濟部中央標準局員工福利委員會印製 苯甲酸， (12) 4-[2-(4-氯苯基磺醯胺基）-5-溴苯甲醯胺基] 苯甲酸， (13) 4-[2-(4-氯苯基磺醯胺基）-5-甲氧基苯甲醯 胺基]苯甲酸， (H)4-[2-(4-溴苯基磺醯胺基）-5-氯苯甲醯胺基] 苯甲酸， 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 39331 523506 _H3 (15) 4-[2-(4-甲基苯基磺醯胺基）-5-氯苯甲醯胺 基]苯甲酸， (16) 4-[2-(4-甲氧基苯基磺醯胺基）-5-氯苯甲醯 胺基]苯甲酸， (Π)4-[2-(4-硝基苯磺醯胺基）-5-氯苯甲醯胺基] 苯甲酸， (18) 4-[2-(2,4-二氯苯磺醯胺基）-5-氯苯甲醯胺 基]苯甲酸， (19) 4-[2-(4-正丁基苯磺醯胺基）-5-氯苯甲醯胺 基]苯甲酸， (20) 4-[2-(4-氯苯磺醯胺基）苯甲醯胺基]苯甲酸 (21) 4-(2-苯磺醯胺基-5-氟苯甲醯胺基）苯甲酸 (22) 4-(2-苯磺醯胺基-4-氟苯甲醯胺基）苯甲酸 (23) 4-[2-(4-氯苯磺醯胺基）-4-氟苯甲醯胺基） 苯甲酸， (24) 4-[2-(4-氟苯磺醯胺基）-5-氯苯甲醯胺基） 經濟部中央標準局員工福利委員會印製 苯甲酸， (25) 4-[2-(4-三氟甲基苯磺醯胺基）-5-氯苯甲醯 胺基)苯甲酸， (26) 4-(2-苯磺醯胺基-5-氯苯甲醯胺基甲基）苯 甲酸， (27) 4-[2-(2-苯基乙烯基)磺醯胺基-5-氯苯甲醯 胺基]苯甲酸， 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 6 39331 523506 _H3 (28) 4-[2-(2-苯基乙基)磺醯胺基-5-氯苯甲醯胺 基]苯甲酸， (29) 4-f2-(4-氯苯磺醯胺基）-5-硝基苯甲醯胺基 ]苯甲酸， (30) 4-[2-(4-羥基苯磺醯胺基）-5-氯苯甲醯胺基 ]苯甲酸， (31) 4-(2-苯磺醯胺基-5-氯苯胺羰基）苯甲酸， (32) 4·[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基 苯甲醯胺基]苯甲酸， (33) 4-[Ν-[2-(4-氯苯磺醯胺基）-5-氯苯基]胺磺 醯基]苯甲酸， (34) 4-(2-苯甲醯胺基-5-氯苯甲醯胺基）苯甲酸 ， (35) 4-(2-丁基磺醯胺基-5-氯苯甲醯胺基）苯甲 酸， (36) 4-[2-(3-氯苯磺醯胺基）苯甲醯胺基]苯甲酸 或 (37) 4-[2-(4-溴苯磺醯胺基）苯甲醯胺基]苯甲酸 及其甲酯。 經濟部中央標準局員工福利委員會印製 10.如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 可接受性塩，係 (1) 4-[2-(4-氯苯磺醯胺基）-5-氯苯氧甲基]苯甲 酸， (2) 4-(2-苯磺醯胺基-5-氯苯氧甲基）苯甲酸， (3) 4-(2-苯磺醯胺基-4-氯苯氧甲基)苯甲酸， (4) 4-[2-(4-氯苯磺醯胺基）-4-氯苯氧甲基]苯甲 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 7 39331 523506 ___H3 酸， (5) 4-[2-(4-氯苯磺醯胺基）-5-氯苯氧甲基]苯甲 酸， (6) 4-(2-苯磺醯胺基-5-三氯甲基苯氧甲基）苯甲 酸， (7) 4-[2-(N-異丙基-苯磺醯胺基）-4-氯苯氧甲基 ]苯甲酸， (8) 4-[2-(N-羧甲基-苯磺醯胺基氯苯氧甲基 ]苯甲酸， (9) 4-[2-[N-(2-羥乙基）-苯磺醯胺基M-氯苯氧 甲基]苯甲酸， (10) 4-[2-(N-甲基-苯磺醯胺基）-4-三氟甲基苯氧 甲基]苯甲酸， (11) 4-[2-[Ν-(2-羥乙基）-苯磺醯胺基]-4-三氟甲 基苯氧甲基]苯甲酸， (12) 4-[2-[N-(2-羥乙基）-苯磺醯胺基]-5-三氟甲 基苯氧甲基]苯甲酸， (13) 4-[2-(N-甲基-苯磺醯胺基）-5-氯苯氧甲基] 苯甲酸， 經濟部中央標準局員工福利委員會印製 (14) 4-[2-[N-(2-羥乙基）-苯磺醯胺基]-5-氯苯氧 甲基]苯甲酸， (15) 4_[2-(N-甲基-苯磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸， (16) 4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]苯甲酸， (17) 4-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧甲基 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 8 39331 523506 _H3 ]苯甲酸， (18) 4-[2-(N-異丙基-苯磺醯胺基Μ-三氟甲基苯 氧甲基]苯甲酸， (19) 4-[2-[Ν-(2-甲氧乙氧甲基）-苯磺醯胺基]-4-氯苯氧甲基]苯甲酸， (20) 4-[2-[Ν-(2-甲氧乙基）-苯磺醯胺基]-4-氯苯 氧甲基]苯甲酸， (21) 4-[2-[Ν-〇(2-甲氧乙氧基）乙基]-苯磺醯胺 基]-4-氯苯氧甲基]苯甲酸， (22) 4-[2-(Ν-乙基-苯磺醯胺基Μ-氯苯氧甲基] 苯甲酸， (23) 4-[2-(Ν-丙基-苯磺醯胺基）-4-氯苯氧甲基] 苯甲酸， (24) 4-[2-(Ν-丁基-苯磺醯胺基Μ-氯苯氧甲基] 苯甲酸， (25) 4-[2-(Ν-戊基-苯磺醯胺基）-4-氯苯氧甲基] 苯甲酸， (26) 4-[2-(Ν-己基-苯磺醯胺基）-4-氯苯氧甲基] 苯甲酸， 經濟部中央標準局員工福利委員會印製 (27) 4-[2-(Ν-〒基-苯磺醯胺基Μ-氯苯氧甲基] 苯甲酸， (28) 4-[2-(Ν-異丙基-苯磺醯胺基）-5-甲基苯氧甲 基]苯甲酸， (29) 4-[2-(Ν-甲基-苯磺醯胺基）-5-甲基苯氧甲基 ]苯甲酸， (30) 4-[2-[Ν-(2-羥乙基）-苯磺醯胺基]-5-甲基苯 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 9 39331 523506 ___H3 氧甲基]苯甲酸， (31) 4-[2-[N-(丙-2-烯基）-苯磺醯胺基M-氯苯 氧甲基]苯甲酸， (32) 4-[2-(N-環戊基-苯磺醯胺基M-氯苯氧甲基 ]苯甲酸， (33) 4-[2-[N-(2-甲氧乙基）-苯磺醯胺基&gt;5-三氟 甲基苯氧甲基]苯甲酸， (34) 4-[2-(N-乙基-苯磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸， (35) 4-[2-(N-丙基-苯磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸， (36) 4-[2-(N-異丁基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]苯甲酸， (37) 4-[2-(N-環戊基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]苯甲酸， (38) 4-[2-[N-(丙-2-烯基）苯磺醯胺基]-5-三氟甲 基苯氧甲基]苯甲酸， (39) 4-[2-[N-(2-甲基丙-2-烯基）苯磺醯胺基]-5-三氟甲基苯氧甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (40) 4-[2-(N-異丙基-4-甲基苯磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (41) 4-〇(N-異丙基-4-氟苯磺醯胺基）-5-三氟甲 基苯氧甲基]苯甲酸， (42) 4-[2-(N-異丙基-4-甲氧基苯磺醯胺基）-5-三 贏甲基苯氧甲基]苯甲酸， (43) 4-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧基] 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 10 39331 523506 Η3 苯甲酸' (44) 3-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧基] 桂皮酸， (45) 反式-4-[2-(N-異丙基-苯磺醯胺基）-5-三氟 甲基苯氧甲基]環己烷甲酸， (46) 4-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧基] 苯乙酸， (47) 4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]桂皮酸， (48) 3-[4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲 基苯氧甲基]苯基]丙酸， (49) 3-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]苯乙酸， (50) 4-[2-(N-異丙基-4-乙氧基苯磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸， (51) 4-[2-(N-異丁基-苯磺醯胺基）-5-甲基苯氧甲 基]苯甲酸， (52) 4-[2-(N-異丙基-苯磺醯胺基）-5-氟苯氧甲基 ]苯甲酸， (53) 4-[2-(N-異丙基-苯磺醯胺基）-5-甲氧苯氧甲 基]苯甲酸， (54) 4-[2·(Ν-丙基-苯磺醯胺基）-5-甲基苯氧甲基 ]苯甲酸， (55) 4-[2-[Ν-(丙-2-儲基）-苯磺醯胺基]-5-甲基 苯氧甲基]苯甲酸， (56) 4-[2-[Ν-(2-甲基丙-2-烯基）-苯磺醯胺基]-, Except for compounds). Printed by the Staff Welfare Committee of the Central Bureau of Standards of the Ministry of Economy ㈣ 赖 Ξ * '(3 represents phenyl, indanyl, naphthyl, Z5 is (DCu alkyl, C2.6 alkenyl, (2) phenyl or C5.6 cycloalkyl, (3) via phenyl Or C5_6 cycloalkyl substituted Cw alkyl or C2.4 alkenyl or phenyl substituted with m (m = 1 to 3) R5 groups. 3. For example, sulfonamide or urea in the first item Derivatives and their pharmaceuticals show basic furanyl, thienyl, or pyridine basic paper sizes applicable to Chinese National Standard (CNS) A4 (210 X 297 mm) 3 39331 523506 H3 or (b) (3 is pyridyl, or (c) Z5 is (1) thienyl or (2) furanyl or thiazolyl which may be substituted by one methyl group. 4. For example, the sulfonamide or urea derivative of item 1 or 3 of the scope of patent application and its medical acceptability塩, where @ is phenyl, naphthyl or cyclohexyl, (3 represents phenyl, indanyl or naphthyl, Z5 is (1) thienyl or (2) furanyl or thiazole which may be substituted by 1 methyl group Base 5. For example, the sulfonamide or urea derivative and any one of its groups in the scope of application for patents 1 or 3 represent heteropharmaceutical acceptability 塩, in which the ring and the other group are carbocyclic rings. 2. Sulfonamide or urea derivative of 2 or 3 and its pharmaceutical acceptability, wherein R2 is a base represented by the formula: CONH, CONH-CHr or NHCO. Printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs For example, the sulfonamide or urea derivative and its pharmaceutical acceptability 塩 in the scope of application for patent 1, 2, or 3, wherein R2 is a group represented by the following formula: 〇, Zn7-〇ν3 alkylene (wherein Z7 Represents 0, S or NZδ (where Z6 is hydrogen or methyl). 8. For example, the sulfonamide or urea derivative and its pharmaceutical acceptability in the scope of patent application No. 1, 2 or 3, where R2 is- CH2CHr, -CH = CH-, or -C Three C-. This paper size is applicable to Chinese National Standard (CNS) A4 (210 X 297 mm) 4 39331 523506 _H3 9. If you apply for sulfonamide in item 1 of the patent scope Or urea derivatives and their pharmaceutically acceptable properties, which are (1) 4- (2-benzenesulfonamido-5-chloromethylformamido) benzoic acid, (2) 3- ( 2-benzenesulfonylaminobenzylamino) benzoic acid, (3) 3- (2-benzenesulfonamido-5-chlorobenzylamino) benzoic acid, (4) 4- (2- Benzenesulfonylaminobenzylamino) benzoic acid, (5) 4- [2- (4-chlorophenyl) sulfonamido-5-chlorobenzylamino] benzoic acid, (6) 4 -[2- (4-chlorophenylsulfonamido) -4-chlorobenzylamino] benzoic acid, (7) 4_ [2- (4-chlorophenylsulfonamido) -6-chloro Benzamidine] benzoic acid, (8) 4- [2- (4-chlorophenylsulfonamido) -3-chlorobenzylamino] benzoic acid, (9) 4- [2- ( 2-chlorophenylsulfonylamino) -5-chlorobenzylamino] benzoic acid, (10) 4- [2- (3-chlorophenylsulfonamido) -5-chlorobenzylamine Based] Benzoic acid, (11) 4- [2- (4-Chlorophenylsulfonamido) -5-fluorobenzylamido] Printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs, (12) 4- [2- (4-chlorophenylsulfonamido) -5-bromobenzylamino] benzoic acid, (13) 4- [2- (4-chlorophenylsulfonamido) -5 -Methoxybenzylamino] benzoic acid, (H) 4- [2- (4-Bromophenylsulfonamido) -5-chlorobenzylamino] benzoic acid, this paper is applicable to China country Standard (CNS) A4 (210 X 297 mm) 39331 523506 _H3 (15) 4- [2- (4-methylphenylsulfonamido) -5-chlorobenzylamido] benzoic acid, ( 16) 4- [2- (4-methoxyphenylsulfonamido) -5-chlorobenzylamido] benzoic acid, (Π) 4- [2- (4-nitrobenzenesulfonamido ) -5-chlorobenzylamino] benzoic acid, (18) 4- [2- (2,4-dichlorobenzenesulfonamido) -5-chlorobenzylamino] benzoic acid, ( 19) 4- [2- (4-n-butylbenzenesulfonamido) -5-chlorobenzylamido] benzoic acid, (20) 4- [2- (4-chlorobenzenesulfonamido) Benzamidine] benzoic acid (21) 4- (2-benzenesulfonamido-5-fluorobenzylamido) benzoic acid (22) 4- (2-benzenesulfonamido-4-fluoro Benzamidine) benzoic acid (23) 4- [2- (4-chlorobenzenesulfonamido) -4-fluorobenzylamino) benzoic acid, (24) 4- [2- (4- Fluorobenylsulfonylamino) -5-chlorobenzidinesulfonyl) Printed by Benzoic Acid, Employee Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs, (25) 4- [2- (4-trifluoromethylsulfenylamine) ) -5-chlorobenzylamino) benzoic acid, (26) 4- (2-benzenesulfonamido-5-chlorobenzylaminomethyl) benzoic acid, (27) 4- [2- (2-phenylethyl Alkenyl) sulfonamido-5-chlorobenzylamido] benzoic acid, this paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 6 39331 523506 _H3 (28) 4- [2 -(2-phenylethyl) sulfoamido-5-chlorobenzylamido] benzoic acid, (29) 4-f2- (4-chlorobenzenesulfenamido) -5-nitrobenzyl Amidino] benzoic acid, (30) 4- [2- (4-Hydroxybenzenesulfonamido) -5-chlorobenzylamido] benzoic acid, (31) 4- (2-benzenesulfonamido Methyl-5-chloroaniline carbonyl) benzoic acid, (32) 4 · [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylbenzylamino] benzoic acid, (33 ) 4- [N- [2- (4-chlorobenzenesulfonylamino) -5-chlorophenyl] aminesulfonyl] benzoic acid, (34) 4- (2-benzylaminosulfonyl-5- Chlorobenzylamino) benzoic acid, (35) 4- (2-butylsulfonamido-5-chlorobenzylamino) benzoic acid, (36) 4- [2- (3-chlorobenzene Sulfamethyl) benzylamino] benzoic acid or (37) 4- [2- (4-bromobenzenesulfonamido) benzylamino] benzoic acid and its methyl ester. Printed by the Staff Welfare Committee of the Central Bureau of Standards of the Ministry of Economic Affairs of the People's Republic of China 10. If the sulfonamide or urea derivative and its pharmaceutical acceptability of item 1 in the scope of the application for patent are (1) Fluorenylamino) -5-chlorophenoxymethyl] benzoic acid, (2) 4- (2-benzenesulfonamido-5-chlorophenoxymethyl) benzoic acid, (3) 4- (2-benzene Sulfamethyl-4-chlorophenoxymethyl) benzoic acid, (4) 4- [2- (4-chlorobenzenesulfonamido) -4-chlorophenoxymethyl] benzyl This paper is applicable to China National Standard (CNS) A4 specification (210 X 297 mm) 7 39331 523506 ___H3 acid, (5) 4- [2- (4-chlorobenzenesulfonylamino) -5-chlorophenoxymethyl] benzoic acid, (6) 4- (2-benzenesulfonamido-5-trichloromethylphenoxymethyl) benzoic acid, (7) 4- [2- (N-isopropyl-benzenesulfonamido)- 4-chlorophenoxymethyl] benzoic acid, (8) 4- [2- (N-carboxymethyl-benzenesulfonylaminochlorophenoxymethyl] benzoic acid, (9) 4- [2- [N -(2-hydroxyethyl) -benzenesulfonylamino M-chlorophenoxymethyl] benzoic acid, (10) 4- [2- (N-methyl-benzenesulfonylamino) -4-trifluoro Methylphenoxymethyl] benzoic acid, (11) 4- [2- [N- (2-hydroxyethyl) -benzenesulfonamido] -4-trifluoromethyl Phenoxymethyl] benzoic acid, (12) 4- [2- [N- (2-hydroxyethyl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzoic acid, (13 ) 4- [2- (N-methyl-benzenesulfonamido) -5-chlorophenoxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (14) 4- [2- [N -(2-hydroxyethyl) -benzenesulfonamido] -5-chlorophenoxymethyl] benzoic acid, (15) 4_ [2- (N-methyl-benzenesulfonamido) -5-tri Fluoromethylphenoxymethyl] benzoic acid, (16) 4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (17) 4- [2- (N-Isopropyl-benzenesulfonamido) -5-chlorophenoxymethyl This paper is sized for China National Standard (CNS) A4 (210 X 297 mm) 8 39331 523506 _H3] benzene Formic acid, (18) 4- [2- (N-isopropyl-benzenesulfonamido M-trifluoromethylphenoxymethyl] benzoic acid, (19) 4- [2- [N- (2- Methoxyethoxymethyl) -benzenesulfonylamino] -4-chlorophenoxymethyl] benzoic acid, (20) 4- [2- [N- (2-methoxyethyl) -benzenesulfonamide Methyl] -4-chlorophenoxymethyl] benzoic acid, (21) 4- [2- [N-〇 (2-methoxyethoxy) ethyl] -benzenesulfonamido] -4-chlorobenzene Oxymethyl] benzene Formic acid, (22) 4- [2- (N-ethyl-benzenesulfonamidoM-chlorophenoxymethyl] benzoic acid, (23) 4- [2- (N-propyl-benzenesulfonamide ) -4-chlorophenoxymethyl] benzoic acid, (24) 4- [2- (N-butyl-benzenesulfonamido M-chlorophenoxymethyl] benzoic acid, (25) 4- [ 2- (N-pentyl-benzenesulfonamido) -4-chlorophenoxymethyl] benzoic acid, (26) 4- [2- (N-hexyl-benzenesulfonamido) -4-chlorobenzene Oxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (27) 4- [2- (N-fluorenyl-benzenesulfonylamino-M-chlorophenoxymethyl] benzoic acid, (28) 4- [2- (N-isopropyl-benzenesulfonamido) -5-methylphenoxymethyl] benzoic acid, (29) 4- [2- (N-methyl-benzenesulfonamido) ) -5-methylphenoxymethyl] benzoic acid, (30) 4- [2- [N- (2-hydroxyethyl) -benzenesulfonamido] -5-methylbenzene Paper size applicable to China National Standard (CNS) A4 Specification (210 X 297 mm) 9 39331 523506 ___H3 oxymethyl] benzoic acid, (31) 4- [2- [N- (prop-2-enyl) -benzenesulfonamido M-chlorophenoxymethyl] benzoic acid, (32) 4- [2- (N-cyclopentyl-benzenesulfonylamino) M-chlorophenoxymethyl] benzoic acid, (33) 4- [2- [N- (2 -Methoxyethyl) -benzenesulfonamido &gt; 5-trifluoromethylphenoxymethyl] benzoic acid, (34) 4- [2- (N-ethyl-benzenesulfonamido) -5 -Trifluoromethylphenoxymethyl] benzoic acid, (35) 4- [2- (N-propyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (36 ) 4- [2- (N-isobutyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (37) 4- [2- (N-cyclopentyl-benzene Sulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (38) 4- [2- [N- (prop-2-enyl) benzenesulfonamido] -5-trifluoro Methylphenoxymethyl] benzoic acid, (39) 4- [2- [N- (2-methylprop-2-enyl) benzenesulfonamido] -5-trifluoromethylphenoxymethyl ] Benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (40) ] Benzoic acid, (41) 4-〇 (N-isopropyl-4-fluorobenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (42) 4- [2- ( N-isopropyl-4-methoxybenzenesulfonylamino) -5-trimethylphenoxymethyl] benzoic acid, (43) 4- [2- (N-isopropyl-benzenesulfonyl) Amine) -5-chlorophenoxy] Applicable for this paper size Chinese National Standard (CNS) A4 (210 X 297 mm) 10 39331 523506 Η3 Benzoic acid '(44) 3- [2- (N-isopropyl-benzenesulfonamido) -5-chlorophenoxy Cinnamic acid, (45) trans-4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] cyclohexanecarboxylic acid, (46) 4- [2- (N-isopropyl-benzenesulfonamido) -5-chlorophenoxy] phenylacetic acid, (47) 4- [2- (N-isopropyl-benzenesulfonamido) -5 -Trifluoromethylphenoxymethyl] cinnamic acid, (48) 3- [4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzene Propyl] propionic acid, (49) 3- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] phenylacetic acid, (50) 4- [2- ( N-isopropyl-4-ethoxybenzenesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, (51) 4- [2- (N-isobutyl-benzenesulfonylsulfonium (Amino) -5-methylphenoxymethyl] benzoic acid, (52) 4- [2- (N-isopropyl-benzenesulfonamido) -5-fluorophenoxymethyl] benzoic acid, ( 53) 4- [2- (N-isopropyl-benzenesulfonylamino) -5-methoxyphenoxymethyl] benzoic acid, (54) 4- [2 · (N-propyl-benzenesulfonyl) Amino) -5-methylphenoxymethyl] benzoic acid, (55 ) 4- [2- [N- (propan-2-yl) -benzenesulfonamido] -5-methylphenoxymethyl] benzoic acid, (56) 4- [2- [Ν- (2 -Methylprop-2-enyl) -benzenesulfonamido]- 經濟部中央標準局員工福利委員會印製 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 11 39331 523506 5-甲基苯氧甲基]苯甲酸， (57) 4-[2-(N-環丙基甲基-苯磺醯胺基）-5-甲基苯 氧甲基]苯甲酸， (58) 4-[2-(N-丙基-苯磺醯胺基）-5-氯苯氧甲基] 苯甲酸， (59) 4-[2-(N-異丁基-苯磺醯胺基）-5-氯苯氧甲基 ]苯甲酸， (60) 4-[2-[N-(丙-2-烯基）-苯磺醯胺基]-5-氯苯 氧甲基]苯甲酸， (61) 4-[2-[N-(2-甲基丙-2-烯基）-苯磺醯胺基]-5-氯苯氧甲基]苯甲酸， (62) 4-[2-(N-環丙基甲基-苯磺醯胺基）-5-氯苯氧 甲基]苯甲酸， (63) 4-[2-(N-甲氧基甲基-苯磺醯胺基）-5-三氟甲 基苯氧甲基]苯甲酸， (64) 4-[2-(N_異丁基-苯磺醯胺基）-4-甲基苯氧甲 基]苯甲酸， (65) 4-[2-(N-異丙基-苯磺醯胺基）-4-甲基苯氧甲 基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (66) 4-[2-[N-(丙-2-烯基）-苯磺醯胺基M-甲基 苯氧甲基]苯甲酸， (67) 4-[2-(N-異丙基-4-乙氧基苯磺醯胺基）-5-氯 苯氧甲基]苯甲酸， (68) 4-[2-(N-異丙基-4-乙氧基苯磺醯胺基）-5-甲 基苯氧甲基]苯甲酸， (69) 4-[2-(N-乙基-苯磺醯胺基）-4-甲基苯氧甲基 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 12 39331 523506 _H3 ]苯甲酸， (70) 4-[2-(N-丙基-苯磺醯胺基）-4-甲基苯氧甲基 ]苯甲酸， (71) 4-[2-(N-丁基-苯磺醯胺基M-甲基苯氧甲基 ]苯甲酸， (72) 4-[2-[N-(2-甲基丙-2-烯基）-苯磺醯胺基]-4-甲基苯氧甲基]苯甲酸， (73) 4-[2-(N-環丙基甲基-苯磺醯胺基）-4-甲基苯 氧甲基]苯甲酸， (74) 4-[2-(N-異丙基-丙磺醯胺基）-5-甲基苯氧甲 基]苯甲酸， (75) 4-[2-(N-異丙基-戊磺醯胺基）-5-甲基苯氧甲 基]苯甲酸， (76) 4-[2-(N-T基-甲磺醯胺基）-5-甲基苯氧甲基 ]苯甲酸， (77) 4-[2-(N-〒基-丙磺醯胺基）-5-甲基苯氧甲基 ]苯甲酸， (78) 4-[2-(N-異丙基-環戊磺醯胺基）-5-甲基苯氧 甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (79) 4-[2-(N-異丁基-乙磺醯胺基）-4-甲基苯氧甲 基]苯甲酸， (80) 4_[2-(N-異丁基-丙磺醯胺基M-甲基苯氧甲 基]苯甲酸， (81) 4-[2-(N-異丁基-丁磺醯胺基M-甲基苯氧甲 基]苯甲酸， (82) 4-[2-(N-異丁基-丙磺醯胺基）-5-甲基苯氧甲 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 13 39331 523506 ___H3 基]苯甲酸， (83) 4-[2-[N-(丙-2-烯基）-丙磺醯胺基]-5-甲基 苯氧甲基]苯甲酸， (84) 4-[2-[N-(2-甲基丙-2-烯基）-丙磺醯胺基]-5-甲基苯氧甲基]苯甲酸， (85) 4-[2-(N-異丁基-苯磺醯胺基）-4-氯-苯氧甲 基]苯甲酸， (86) 4-[2-(N-丙基-丙磺醯胺基）-5-甲基苯氧甲基 ]苯甲酸， (87) 4-[2-(N-異丁基-己磺醯胺基）-4-甲基苯氧甲 基]苯甲酸， (88) 4-[2-(N-異丁基-戊磺醯胺基）-4-甲基苯氧甲 基]苯甲酸， (89) 4-[2-[N-(丙-2-烯基）-丙磺醯胺基]-5-三氟 甲基苯氧甲基]苯甲酸， (90) 4-[2-[N-(2-甲基丙-2-烯基）-丙磺醯胺基]-5-三氟甲基苯氧甲基]苯甲酸， (91) 4-[2-(N-丙基-丙磺醯胺基）-5-三氟甲基苯氧 甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (92) 4-[2-(N-異丁基-丙磺醯胺基）-5-三氟甲基苯 氧甲基]苯甲酸， (93) 4-[2-(N-丙基-苯磺醯胺基）-5-甲基苯氧甲基 ]桂皮酸， (94) 4-[2-(N-異丁基-苯磺醯胺基）-5-甲基苯氧甲 基]桂皮酸， (95) 4-[2-(N-異丁基-丙磺醯胺基）-5-三氟甲基苯 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 14 39331 523506 _ H3 氧甲基]桂皮酸， (96) 4-[2-(N-甲基-苯磺醯胺基）-5-三氟甲基苯氧 甲基]桂皮酸， (97) 4-[2-(N-丙基-苯磺醯胺基）-5-三氟甲基苯氧 甲基]桂皮酸， (98) 4-[2-(N-異丁基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]桂皮酸， (99) 4-[2-(N-異丙基-丙磺醯胺基）-5-甲基苯氧甲 基]桂皮酸， (100) 4-[2-(N-乙基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]桂皮酸， (101) 4-[2-(N-環丙基甲基-苯磺醯胺基）-5-三氟 甲基苯氧甲基]桂皮酸， (102) 4-[2-(N-異丙基-甲磺醯胺基）-5-三氟甲基 苯氧甲基]桂皮酸， (103) 4-[2-(N-T基-丙磺醯胺基）-5-三氟甲基苯 氧甲基]桂皮酸， (104) 4-[2-(N-丙基-苯磺醯胺基）-4-甲基苯氧甲 基]桂皮酸， 經濟部中央標準局員工福利委員會印製 (105) 4-[2-[N-(丙-2-烯基）-苯磺醯胺基]-5-三氟 甲基苯氧甲基]桂皮酸， (106) 4-[2-[N-(2-甲基丙-2-烯基）-苯磺醯胺基] -5-三氟甲基苯氧甲基]桂皮酸， (107) 4-[2-(N-異丁基-苯磺醯胺基）-4-甲基苯氧 甲基]桂皮酸， (108) 4-[2-(N-〒基-甲磺醯胺基）-5-三氟甲基苯 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 15 39331 523506 __H3 氧甲基]桂皮酸， (109) 4-[2-(N-異丙基-苯磺醯胺基）-4-三氟甲基 苯氧甲基]桂皮酸， (110) 4-[2-(N-異丁基-4-乙氧基苯磺醯胺基）-5-三氟甲基苯氧甲基]苯甲酸， (111) 4-[2-(Ν-甲基·苯磺醯胺基M-氯苯氧甲基] 苯甲酸， (112) 4-[2-(N-環戊基甲基-苯磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (113) 4-[2-(N-環丙基甲基-苯磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (114) 4-[2·(Ν-第三丁基甲基-苯磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸， (115) 4-[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基 苯氧甲基]苯乙酸， (116) 4-[2-(Ν-異丙基-丙磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， (117) 4-[2-(Ν-異丙基-戊磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (118) 4-[2-(Ν-異丙基·丁磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， (119) 4-[2-(Ν-異丙基-己磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， (120) 4-[2-(Ν-異丙基-庚磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， (121) 4-[2-(Ν-異丙基-4-羥基苯磺醯胺基）-5-三 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 16 39331 523506 _H3 氟甲基苯氧甲基]苯甲酸， (122) 4-[2-(N-異丙基-丁磺醯胺基）-5-甲基苯氧 甲基]苯甲酸， (123) 4-[2-(N-異丙基-己磺醯胺基）-5-甲基苯氧 甲基]苯甲酸， (124) 4-[2-(N-異丙基-庚磺醯胺基）-5-甲基苯氧 甲基]苯甲酸， (125) 4-[2-(N-異丙基-甲磺醯胺基）-5-甲基苯氧 甲基]苯甲酸， (126) 4-[2-(N-異丙基-乙磺醯胺基）-5-甲基苯氧 甲基]苯甲酸， (127) 4-[2-(N-異丙基-2-苯基乙磺醯胺基）-5-甲 基苯氧甲基]苯甲酸， (128) 4-[2-(N-異丙基-T基磺醯胺基）-5-甲基苯 氧甲基]苯甲酸， (129) 4-[2-(N-第三丁基甲基-苯磺醯胺基）-4-甲 基苯氧甲基]苯甲酸， (130) 4-[2-(N-異丙基-甲磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (131) 4-[2-(N-異丙基-乙磺醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， (132) 4-[2-(N-異丙基-環戊基甲磺醯胺基）-5-甲 基苯氧甲基]苯甲酸， (133) 4-[2-(N-環己基甲基-丙磺醯胺基）-5-甲基 苯氧甲基]苯甲酸， (134) 4-[2-(N-環戊基甲基-丙磺醯胺基）-5-甲基 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 17 39331 523506 _；_H3 苯氧甲基]苯甲酸， (135) 4-[2-(N-異丙基-丙磺醯胺基）-5-三氟甲基 苯氧甲基]桂皮酸， (136) 4-[2-(N-異丙基-戊磺醯胺基）-5-三氟甲基 苯氧甲基]桂皮酸， (137) 4-[2-(N-異丙基-4-氯苯磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (138) 4-[2-(N-異丙基-4-乙基苯磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸， (139) 4-[2-(N-異丙基-4-丙基苯磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸， (140) 4-[2-(N-異丙基-4-丁基苯磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸， (141) 4-(2-苯磺醯胺基苯氧甲基）苯甲酸， (142) 4-[2-(4-氯苯磺醯胺基）苯氧甲基]苯甲酸， (143) 4-(2-苯磺醯胺基-4-氟苯氧甲基）苯甲酸， (144) 4-(2-苯磺醯胺基-5-氟苯氧甲基）苯甲酸， (145) 4-(2-苯磺醯胺基-4-溴苯氧甲基）苯甲酸， (146) 4-(2-苯磺醯胺基-5-氯苯硫甲基）苯甲酸， 經濟部中央標準局員工福利委員會印製 (147) 4-(2-苯磺醯胺基-4-甲氧苯氧甲基）苯甲酸 (148) 4-(2-苯磺醯胺基-4-三氟甲基苯氧甲基）苯 甲酸， (149) 4-(2-苯磺醯胺基-4-甲基苯氧甲基）苯甲酸， (150) 4-(2-苯磺醯胺基-5-甲基苯氧甲基）苯甲酸， (151) 4-(2-苄磺醯胺基-5-氯苯氧甲基）苯甲酸， 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 18 39331 523506 _H3 (152) 4-(2-苯磺醯胺基-5-甲氧苯氧甲基）苯甲酸， (153) 3-(2-苯磺醯胺基-5-氯苯氧甲基）苯甲酸， (154) 4-(2-苯磺醯胺基-4-氯-5-甲基苯氧甲基）苯 甲酸， (155) 4-(2-苯磺醯胺基-4,5-二氯苯氧甲基）苯甲 酸， (156) 4-(2-苯磺醯胺基_5_氯苯氧甲基）苯二甲酸， (157) 4-(2-苯磺醯胺基-5-氯苯氧基）苯甲酸， (158) 4-[3-(2-苯磺醯胺基-5-氯苯氧基）丙基]苯 甲酸， (159) 反式-4-(2-苯磺醯胺基-5-氯苯氧甲基）環己 烷甲酸， (160) 順式-4-(2-苯磺醯胺基-5-氯苯氧甲基）環己 烷甲酸， (161) 4-[lRS-(2-苯磺醯胺基-5·氯苯氧基）乙基] 苯甲酸， (162) 4-[2-[N-(2-羥基-2-甲基丙基）-苯磺醯胺基 ]-5-三氟甲基苯氧甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (163) 4-[2-[N-(2-羥基-2-甲基丙基）-苯磺醯胺基 ]-5-三氟甲基苯氧甲基]桂皮酸， (164) 4-[2-[N-(2-羥基-2-甲基丙基）-苯磺醯胺基 ]-5-甲基苯氧甲基]苯甲酸， (165) 4-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基 苯氧甲基]苯氧乙酸， (166) 4-[2-(N-異丙基-苯磺醯胺基）-5-甲基苯氧 甲基]苯氧乙酸， 本紙張尺度適用中國國家標準（CNS ) A4規格（210 X 297公釐） 19 39331 523506 _H3 (167) 4-[2-(N-異丙基-苯磺醯胺基）-5-甲基苯氧 甲基]桂皮酸， (168) 4-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧甲 基]苯氧乙酸， (169) 4-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧甲 基]桂皮酸， (170) 4-[2-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲 基苯氧基]乙基]苯甲酸， (171) 2-甲氧基-4-[2-(N-異丙基-苯磺醯胺基-5-三氟甲基苯氧甲基]苯甲酸， (172) 2-羥基-4-[2-(N-異丙基-苯磺醯胺基-5-三 氟甲基苯氧甲基]苯甲酸， (173) 2-羥基-4-[2-(N-異丙基-苯磺醯胺基-5-甲 基苯氧甲基]苯甲酸， (174) 2-羥基-4-〇(Ν·異丙基-苯磺醯胺基-5-氯 苯氧甲基]苯甲酸， (175) 4-[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基 苯胺基甲基]苯甲酸， 經濟部中央標準局員工福利委員貪印製 (176) 4-[Ν-甲基-[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基苯基]胺甲基]苯甲酸， (177) 4-[2-[Ν-(1，3-二羥基丙-2-基）苯磺醯胺基] -5-三氟甲基苯氧甲基]苯甲酸， (178) 4-[2-[Ν-(1，3-二甲氧-2-基）苯磺醯胺基] -5-三氟甲基苯氧甲基]苯甲酸， (179) 4-[2-(Ν-異丙基-2-己烯基磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸， 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 20 39331 523506 Η3 (180) 4-[2-(N-異丙基-環戊基磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (181) 4-[2-(N-異丙基·環己基磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (182) 4-[2-(N-異丙基-環己基磺醯胺基）-5-甲基 苯氧甲基]苯甲酸， (183) 4-[2-(N-異丙基-異丙基磺醯胺基）-5-三氟 甲基苯氧甲基]苯甲酸， (184) 4-[2-(N-異丙基-異丙基磺醯胺基）-5-甲基 苯氧甲基]苯甲酸， (185) 4-[2-(N-異丙基-異丙基磺醯胺基）-5-三氟 甲基苯氧甲基]桂皮酸， (186) 4-[2-(N-異丙基-環戊基磺醯胺基）-5-三氟 甲基苯氧甲基]桂皮酸， (187) 4-[2-(N-異丙基-環己基磺醯胺基）·5-三氟 甲基苯氧甲基]桂皮酸， (188) 4-[2-[Ν-(Ν，Ν-二甲胺基羰甲基）-苯磺醯胺 基]-5-三氟甲基苯氧甲基]苯甲酸， (189) 4-(2-苯磺醯胺基-5-異丙基苯氧甲基）苯甲 經濟部中央標準局員工福利委員會印製 酸， (190) 4-(2-苯磺醯胺基-5-乙基苯氧甲基）苯甲酸， (191) 4-(2-苯磺醯胺基-5-羥甲基苯氧甲基）苯甲 酸， (192) 4-(2-苯磺醯胺基甲基-5-氯苯氧甲基）苯甲 酸， (193) 4-[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 21 39331 523506 H3 經濟部中央標準局員工福利委員會印製 苯氧甲基]苯丙酸， (194) 4-(2-苯磺醯胺基-4-氯苯氧甲基）苯甲醇， (195) 4-(2-苯甲醯胺基-5-氯苯氧甲基）苯甲酸， (196) 4-[2-(N-異丙基-苯磺醯胺基）-5-異丙基苯 氧甲基]苯甲酸， (197) 4-[2-(N-甲基-苯磺醯胺基）-5-異丙基苯氧 甲基]苯甲酸， (198) 4-[2-(N-異丙基-苯磺醯胺基）-5-乙基苯氧 甲基]苯甲酸， (199) 4-[2-(N-異丙基-4-丙氧基苯磺醯胺基）-5-三氟甲基苯氧甲基]苯甲酸， (200) 4-[2-(N-異丙基-4-乙硫基苯磺醯胺基）-5-三氟甲基苯氧甲基]苯甲酸， (201) 4-[2-(N-異丙基-4-甲硫基苯磺醯胺基）-5-三氟甲基苯氧甲基]苯甲酸， (202) 4-[2-(N-異丙基-4-丁氧基苯磺醯胺基）-5-三氟甲基苯氧甲基]苯甲酸， (203) 4-[2-(N-異丙基-4-異丙氧基苯磺醯胺基）-5-三氟甲基苯氧甲基]苯甲酸， (204) 4-[2-(N-異丁基-苯甲醯胺基）-5-氯苯氧甲 基]苯甲酸， (205) 4-[2-(N-異丙基-苯甲醯胺基）-5-三氟甲基 苯氧甲基]苯甲酸， (206) 6-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基 苯氧甲基]-2-萘甲酸， (207) 4-[2-(N-異丙基-丁醯胺基）-5-三氟甲基苯 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 22 39331 523506 _H3 氧甲基]桂皮酸， (208) 4-[2·(Ν-異丙基-4-乙氧苯磺醯胺基）-5-三 氟甲基苯氧甲基]桂皮酸， (209) 4-[2-(Ν-異丁基-4-乙氧苯磺醯胺基）-5-三 氟甲基苯氧甲基]桂皮酸或 (210) 4-[2-(Ν-異丙基-3-乙氧苯磺醯胺基）-5-三 氟甲基苯氧甲基]苯甲酸或其甲酯。 11. 如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 可接受性塩，係 (1) 4-[2-|&gt;(4-氯苯磺醯胺基）-5-氯苯基]-(Ε)-乙烯基]苯甲酸， (2) 4-[2-[2-(4-氯苯磺醯胺基)-5-氯苯基ΜΖ)-乙烯基]苯甲酸， (3) 4-[2-[2-(4-氯苯基)磺醯胺基-5-氯苯基]乙基 ]苯甲酸， (4) 4-[2-[2-(4-氯苯磺醯胺基）-5-氯苯基]乙炔基 ]苯甲酸， (5) 4-[2-[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基 苯基]乙基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (6) 4-[2-[2-(Ν-異丙基-苯磺醯胺基）-5-三氟甲基 苯基ME)-乙烯基]苯甲酸或 (7) 4-[2-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基 苯基]-(Ζ)-乙烯基]苯甲酸或其甲酯。 12. 如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 可接受性塩，係 (1)4-[2-(Ν-異丙基-2-噻吩基磺醯胺基）-5-氯苯 本紙張尺度適用中國國家標準（CNS) Α4規格（210 X 297公釐） 23 39331 523506 _ H3 氧甲基]苯甲酸， (2) 4-[2-(N-異丙基-2-噻吩基磺醯胺基）-5-甲基 苯氧甲基]苯甲酸， (3) 4-[2-(N-異丙基-2-呋喃基磺醯胺基）-5-甲基 苯氧甲基]苯甲酸， (4) 4-[2-(N-異丙基-2-呋喃基磺醯胺基）-5-氯苯 氧甲基]苯甲酸， (5) 4-[2-(N-丙基-2-呋喃基磺醯胺基）-5-三氟甲 基苯氧甲基]桂皮酸， (6) 4-[2-(N-丙基-2-呋喃基磺醯胺基）-5-甲基苯 氧甲基]苯甲酸， (7) 4-[2-[N-(異丁基-2-呋喃基磺醯胺基）-5-甲基 苯氧甲基]苯甲酸， (8) 4_[2-[N-(異丁基-2-呋喃基磺醯胺基）-5-三氟 甲基苯氧甲基]桂皮酸， (9) 4-[2-[N-(丙-2-烯基）-2-呋喃基磺醯胺基]-5-甲基苯氧甲基]苯甲酸， (10) 4-[2-[N-(2-甲基丙-2-烯基）-2-呋喃基磺醯 胺基]-5-甲基苯氧甲基]苯甲酸， 經濟部中央標準局員工福利委員會印製 (11) 4-[2-(Ν-異丁基-2-呋喃基磺醯胺基）-4-甲基 苯氧甲基]苯甲酸， (12) 4-[2-(N-異丙基-2-呋喃基磺醯胺基）-4-甲基 苯氧甲基]苯甲酸， (13) 4-[2-[N-(2-甲基丙-2-烯基）-2-呋喃基磺醯 胺基)-4-甲基苯氧甲基]苯甲酸， (14) 4-[2-N-異丙基-2-呋喃基磺醯胺基-5-甲基苯 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 24 39331 523506 氧甲基]桂皮酸， (15) 4-[2-N-異丙基-2-呋喃基磺醯胺基-5-三氟甲 基苯氧甲基]桂皮酸， (16) 4-[2-N-異丙基-2-呋喃基磺醯胺基-4-三氟甲 基苯氧甲基]苯甲酸， (17) 4-[2-N-異丁基-2-呋喃基磺醯胺基-4-三氟甲 基苯氧甲基]苯甲酸， (18) 4-[2-N-異丁基-2-呋喃基磺醯胺基-5-氯苯氧 甲基]苯甲酸， (19) 4-[2-N-異丙基-2-呋喃基磺醯胺基-5-氯苯氧 甲基]桂皮酸， (20) 4-[2-N-異丁基-2-呋喃基磺醯胺基-5-氯苯氧 甲基]桂皮酸， (21) 4-[2-N-異丁基-2-呋喃基磺醯胺基-5-三氟甲 基苯氧甲基]苯甲酸， (22) 4-[2-N-異丁基-2-呋喃基磺醯胺基-4-氯苯氧 甲基]苯甲酸， (23) 4-[2-N-異丁基-2-呋喃基磺醯胺基-4-甲基苯 氧甲基]桂皮酸， 經濟部中央標準局員工福利委員會印製 (24) 4-[2-N-異丙基-2-呋喃基磺醯胺基-5-三氟甲 基苯氧甲基]苯甲酸， (25) 4-[2-N-異丙基-2-噻吩基磺醯胺基-5-三氟甲 基苯氧甲基]苯甲酸， (26) 4-[2-[N-(2-羥基-2-甲基丙基）-2-噻吩基磺 醯胺基]-5-三氟甲基苯氧甲基]苯甲酸， (27) 4-[2-(N-異丙基-2-呋喃醯胺基）-5-三氟甲基 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 25 39331 523506 _H3 苯氧甲基]苯甲酸， (28) 4-[2-(2-噻吩基磺醯胺基）-5-氯苯甲醯胺基] 苯甲酸， (29) 4-[2-(N-異丙基-2-呋喃基磺醯胺基）-5-甲基 苯硫甲基）苯甲酸， (30) 4-[2-(N-異丁基-2-噻吩基磺醯胺基）-5-三氟 甲基苯氧甲基]桂皮酸， (31) 4-[2-(N-異丙基-2-呋喃醯胺基）-5-三氟甲基 苯氧甲基]桂皮酸或 (32) 4-[2-(N-異丁基-2-呋喃醯胺基）-5-三氟甲基 苯氧甲基]桂皮酸或其甲酯。 Π.如申請專利範圍第1項之磺醯胺或脲衍生物及其醫藥 可接受性塩，係 (1) 5-[2-(Ν-異丙基-苯磺醯胺基）-5-甲基苯氧甲 基]呋喃-2-羧酸， (2) 6-(2-苯磺醯胺基-5-氯苯氧甲基）菸鹼酸， (3) 5-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]噻吩-2-羧酸， 經濟部中央標準局員工福利委員會印製 (4) 5-[2-(N-異丙基-苯磺醯胺基）-5-三氟甲基苯 氧甲基]呋喃-2-羧酸， (5) 5-[2-(N-異丙基-苯磺醯胺基）-5-甲基苯氧甲 基]噻吩-2-羧酸， (6) 5-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧甲基] 噻吩-2-羧酸， (7) 5-[2-(N-異丙基-苯磺醯胺基）-5-氯苯氧甲基] 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 26 39331 523506 __H3_ 呋喃-2-竣酸或 (8)4-(3-苯磺醯胺基-5-三氟甲基吡啶-2-基氧甲 基）苯甲酸，或其甲酯。 14. 如申請專利範圍第1項之化合物，其中之化合物，其中 之化合物係 (1) 4-[3-(N-異丙基-5-甲基-2-呋喃基磺醯胺基）萘醯-2-基氧基甲基]桂皮酸、 (2) 4-[6-(N-甲基-5-甲基-2-呋喃基磺醯胺基）茚滿-5-基氧基甲基]桂皮酸或 (3) 3-甲基-4-[2-(N-甲基-(4-甲基-2-噻吩基磺醯基）胺 基）-4,5-二甲基苯氧基甲基]苯甲酸或該等化合物之甲酯。 15. —種前列腺素E2拮抗或激動劑之醫藥組成物，其含有如申 請專利範圍第1項所示之通式（1)之磺醯胺或脲衍生物或其 醫藥可接受性塩作爲有效成分。 經濟部中央標準局員工福利委員會印製 本紙張尺度適用中國國家標準（CNS) A4規格（210 X 297公釐） 27 39331Printed by the Staff Welfare Committee of the Central Bureau of Standards of the Ministry of Economic Affairs This paper is printed in accordance with the Chinese National Standard (CNS) A4 (210 X 297 mm) 11 39331 523506 5-methylphenoxymethyl] benzoic acid, (57) 4- [ 2- (N-cyclopropylmethyl-benzenesulfonamido) -5-methylphenoxymethyl] benzoic acid, (58) 4- [2- (N-propyl-benzenesulfonamido) -5-chlorophenoxymethyl] benzoic acid, (59) 4- [2- (N-isobutyl-benzenesulfonamido) -5-chlorophenoxymethyl] benzoic acid, (60) 4- [2- [N- (prop-2-enyl) -benzenesulfonamido] -5-chlorophenoxymethyl] benzoic acid, (61) 4- [2- [N- (2-methylpropane -2-alkenyl) -benzenesulfonylamino] -5-chlorophenoxymethyl] benzoic acid, (62) 4- [2- (N-cyclopropylmethyl-benzenesulfonylamino) -5 -Chlorophenoxymethyl] benzoic acid, (63) 4- [2- (N-methoxymethyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (64 ) 4- [2- (N-isobutyl-benzenesulfonylamino) -4-methylphenoxymethyl] benzoic acid, (65) 4- [2- (N-isopropyl-benzenesulfonyl) Amine) -4-methylphenoxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (66) 4- [2- [N- (prop-2-enyl) -benzenesulfonate醯 Amino M-methylphenoxymethyl] benzoic acid, (67) 4- [2- (N-isopropyl-4-ethoxybenzenesulfonamido) -5-chlorophenoxymethyl] Benzoic acid, (68) 4- [2- (N-isopropyl-4-ethoxybenzenesulfonamido) -5-methylphenoxymethyl] benzoic acid, (69) 4- [2- (N-ethyl-benzenesulfonamido) -4-methylphenoxymethyl This paper is sized to the Chinese National Standard (CNS) A4 (210 X 297 mm) 12 39331 523506 _H3] benzoic acid, (70) 4- [2- (N-propyl-benzenesulfonylamino) -4-methylphenoxymethyl] benzoic acid, (71) 4- [2- (N-butyl-benzenesulfonylamino) M -Methylphenoxymethyl] benzoic acid, (72) 4- [2- [N- (2-methylprop-2-enyl) -benzenesulfonamido] -4-methylphenoxymethyl ] Benzoic acid, (73) 4- [2- (N-cyclopropylmethyl-benzenesulfonamido) -4-methylphenoxymethyl] benzoic acid, (74) 4- [2- (N -Isopropyl-propanesulfonylamino) -5-methylphenoxymethyl] benzoic acid, (75) 4- [2- (N-isopropyl-pentylsulfonylamino) -5-methyl Phenoxymethyl] benzoic acid, (76) 4- [2- (NT-Methanesulfonylamino) -5-methylphenoxymethyl] benzoic acid, (77) 4- [2- (N- Fluorenyl-propanesulfonylamino) -5-methylphenoxy Methyl] benzoic acid, (78) 4- [2- (N-isopropyl-cyclopentanesulfonamido) -5-methylphenoxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (79) 4- [2- (N-isobutyl-ethanesulfonamido) -4-methylphenoxymethyl] benzoic acid, (80) 4_ [2- (N-isobutyl-propyl Sulfonamido M-methylphenoxymethyl] benzoic acid, (81) 4- [2- (N-isobutyl-butanesulfonamido M-methylphenoxymethyl] benzoic acid, (82 ) 4- [2- (N-isobutyl-propanesulfonylamino) -5-methylphenoxymethyl This paper is sized for the Chinese National Standard (CNS) A4 (210 X 297 mm) 13 39331 523506 ___H3 Yl] benzoic acid, (83) 4- [2- [N- (prop-2-enyl) -propanesulfenylamino] -5-methylphenoxymethyl] benzoic acid, (84) 4- [ 2- [N- (2-methylprop-2-enyl) -propanesulfonylamino] -5-methylphenoxymethyl] benzoic acid, (85) 4- [2- (N-isobutyl -Phenylsulfonylamino) -4-chloro-phenoxymethyl] benzoic acid, (86) 4- [2- (N-propyl-propanesulfonylamino) -5-methylphenoxymethyl ] Benzoic acid, (87) 4- [2- (N-isobutyl-hexanesulfonamido) -4-methylphenoxymethyl] benzoic acid, (88) 4- [2- (N-iso Butyl-pentylsulfonium ) -4-methylphenoxymethyl] benzoic acid, (89) 4- [2- [N- (prop-2-enyl) -propanesulfenylamino] -5-trifluoromethylphenoxy Methyl] benzoic acid, (90) 4- [2- [N- (2-methylprop-2-enyl) -propanesulfonylamino] -5-trifluoromethylphenoxymethyl] benzoic acid , (91) 4- [2- (N-propyl-propanesulfenylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (92) 4 -[2- (N-isobutyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, (93) 4- [2- (N-propyl-benzenesulfonylamine) ) -5-methylphenoxymethyl] cinnamic acid, (94) 4- [2- (N-isobutyl-benzenesulfonamido) -5-methylphenoxymethyl] cinnamic acid, ( 95) 4- [2- (N-isobutyl-propanesulfonylamino) -5-trifluoromethylbenzene This paper is sized for China National Standard (CNS) A4 (210 X 297 mm) 14 39331 523506 _ H3 oxymethyl] cinnamic acid, (96) 4- [2- (N-methyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (97) 4- [ 2- (N-propyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (98) 4- [2- (N-isobutyl-benzenesulfonamido) -5- three Methylphenoxymethyl] cinnamic acid, (99) 4- [2- (N-isopropyl-propanesulfonylamino) -5-methylphenoxymethyl] cinnamic acid, (100) 4- [ 2- (N-ethyl-benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid, (101) 4- [2- (N-cyclopropylmethyl-benzenesulfonylamine) ) -5-trifluoromethylphenoxymethyl] cinnamic acid, (102) 4- [2- (N-isopropyl-methanesulfonylamino) -5-trifluoromethylphenoxymethyl] Cinnamic acid, (103) 4- [2- (NT-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid, (104) 4- [2- (N-propyl- Phenylsulfonylamino) -4-methylphenoxymethyl] cinnamic acid, printed by (105) 4- [2- [N- (prop-2-enyl) -benzene Sulfonylamino] -5-trifluoromethylphenoxymethyl] cinnamic acid, (106) 4- [2- [N- (2-methylprop-2-enyl) -benzenesulfonylamino] -5-trifluoromethylphenoxymethyl] cinnamic acid, (107) 4- [2- (N-isobutyl-benzenesulfonamido) -4-methylphenoxymethyl] cinnamic acid, ( 108) 4- [2- (N-fluorenyl-methanesulfonylamino) -5-trifluoromethylbenzene This paper is sized for China National Standard (CNS) A4 (210 X 297 mm) 15 39331 5235 06 __H3 oxymethyl] cinnamic acid, (109) 4- [2- (N-isopropyl-benzenesulfonamido) -4-trifluoromethylphenoxymethyl] cinnamic acid, (110) 4- [2- (N-isobutyl-4-ethoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (111) 4- [2- (N-methyl · Benzenesulfonylamino-M-chlorophenoxymethyl] benzoic acid, (112) 4- [2- (N-cyclopentylmethyl-benzenesulfonylamino) -5-trifluoromethylphenoxymethyl ] Benzoic acid, (113) 4- [2- (N-cyclopropylmethyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (114) 4- [2 · (N-third butylmethyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (115) 4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenoxymethyl] phenylacetic acid, (116) 4- [2- (N-isopropyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid , (117) 4- [2- (N-Isopropyl-pentylsulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (118) 4- [2- (N-isopropylbutanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, (119) 4- [2- (N-isopropyl-hexanesulfonate Amidine ) -5-trifluoromethylphenoxymethyl] benzoic acid, (120) 4- [2- (N-isopropyl-heptylsulfonamido) -5-trifluoromethylphenoxymethyl] benzene Formic acid, (121) 4- [2- (N-isopropyl-4-hydroxybenzenesulfonamido) -5-three paper sizes applicable to China National Standard (CNS) A4 (210 X 297 mm) 16 39331 523506 _H3 fluoromethylphenoxymethyl] benzoic acid, (122) 4- [2- (N-isopropyl-butanesulfonylamino) -5-methylphenoxymethyl] benzoic acid, (123 ) 4- [2- (N-isopropyl-hexanesulfonamido) -5-methylphenoxymethyl] benzoic acid, (124) 4- [2- (N-isopropyl-heptanesulfonyl) (Amino) -5-methylphenoxymethyl] benzoic acid, (125) 4- [2- (N-isopropyl-methanesulfonylamino) -5-methylphenoxymethyl] benzoic acid, (126) 4- [2- (N-isopropyl-ethanesulfonamido) -5-methylphenoxymethyl] benzoic acid, (127) 4- [2- (N-isopropyl-2 -Phenylethanesulfonylamino) -5-methylphenoxymethyl] benzoic acid, (128) 4- [2- (N-isopropyl-Tylsulfonamido) -5-methylbenzene Oxymethyl] benzoic acid, (129) 4- [2- (N-Third-butylmethyl-benzenesulfonamido) -4-methylphenoxymethyl] benzoic acid, (130) 4- [2- (N-iso -Methanesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, printed by the Employee Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (131) 4- [2- (N-isopropyl-ethanesulfonate) Fluorenylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, (132) 4- [2- (N-isopropyl-cyclopentylmethanesulfonamido) -5-methylphenoxy Methyl] benzoic acid, (133) 4- [2- (N-cyclohexylmethyl-propanesulfonylamino) -5-methylphenoxymethyl] benzoic acid, (134) 4- [2- ( N-cyclopentylmethyl-propanesulfonylamino) -5-methyl This paper size applies to Chinese National Standard (CNS) A4 (210 X 297 mm) 17 39331 523506 _; _ H3 phenoxymethyl] benzoic acid , (135) 4- [2- (N-isopropyl-propanesulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid, (136) 4- [2- (N-isopropyl -Pentylsulfonylamino) -5-trifluoromethylphenoxymethyl] cinnamic acid, (137) 4- [2- (N-isopropyl-4-chlorobenzenesulfonylamino) -5- Trifluoromethylphenoxymethyl] benzoic acid, (138) 4- [2- (N-isopropyl-4-ethylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzene Formic acid, (139) 4- [2- (N-isopropyl-4-propylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl ] Benzoic acid, (140) 4- [2- (N-isopropyl-4-butylbenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (141) 4- ( 2-benzenesulfonylaminophenoxymethyl) benzoic acid, (142) 4- [2- (4-chlorobenzenesulfonamido) phenoxymethyl] benzoic acid, (143) 4- (2-benzene Sulfamethyl-4-fluorophenoxymethyl) benzoic acid, (144) 4- (2-phenylsulfoamino-5-fluorophenoxymethyl) benzoic acid, (145) 4- (2-benzene Sulfonamido-4-bromophenoxymethyl) benzoic acid, (146) 4- (2-benzenesulfonamido-5-chlorophenylthiomethyl) benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (147) 4- (2-benzenesulfenamido-4-methoxyphenoxymethyl) benzoic acid (148) 4- (2-benzenesulfenamido-4-trifluoromethylphenoxymethyl) ) Benzoic acid, (149) 4- (2-benzenesulfonamido-4-methylphenoxymethyl) benzoic acid, (150) 4- (2-benzenesulfonamido-5-methylphenoxy) Methyl) benzoic acid, (151) 4- (2-benzylsulfonamido-5-chlorophenoxymethyl) benzoic acid, this paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 18 39331 523506 _H3 (152) 4- (2-benzenesulfonamido-5-methoxyphenoxymethyl) benzene Acid, (153) 3- (2-benzenesulfenamido-5-chlorophenoxymethyl) benzoic acid, (154) 4- (2-benzenesulfenamido-4-chloro-5-methylbenzene Oxymethyl) benzoic acid, (155) 4- (2-benzenesulfonamido-4,5-dichlorophenoxymethyl) benzoic acid, (156) 4- (2-benzenesulfonamido_5 _Chlorophenoxymethyl) phthalic acid, (157) 4- (2-benzenesulfonamido-5-chlorophenoxy) benzoic acid, (158) 4- [3- (2-benzenesulfonamide Methyl-5-chlorophenoxy) propyl] benzoic acid, (159) trans-4- (2-benzenesulfonamido-5-chlorophenoxymethyl) cyclohexanecarboxylic acid, (160) cis 4- (2-benzenesulfonamido-5-chlorophenoxymethyl) cyclohexanecarboxylic acid, (161) 4- [lRS- (2-benzenesulfonamido-5 · chlorophenoxy) ethyl Phenyl] benzoic acid, (162) 4- [2- [N- (2-hydroxy-2-methylpropyl) -benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzoic acid, Printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (163) 4- [2- [N- (2-hydroxy-2-methylpropyl) -benzenesulfonylamino] -5-trifluoromethylphenoxymethyl Methyl] cinnamic acid, (164) 4- [2- [N- (2-hydroxy-2-methylpropyl) -benzenesulfonamido] -5-methylphenoxymethyl] benzoic acid, (165 ) 4- [2- (N-isopropyl- Sulfonylamino) -5-trifluoromethylphenoxymethyl] phenoxyacetic acid, (166) 4- [2- (N-isopropyl-phenylsulfonamido) -5-methylphenoxymethyl Based] phenoxyacetic acid, this paper size applies Chinese National Standard (CNS) A4 (210 X 297 mm) 19 39331 523506 _H3 (167) 4- [2- (N-isopropyl-benzenesulfonylamino) -5-methylphenoxymethyl] cinnamic acid, (168) 4- [2- (N-isopropyl-benzenesulfonamido) -5-chlorophenoxymethyl] phenoxyacetic acid, (169) 4- [2- (N-isopropyl-benzenesulfonamido) -5-chlorophenoxymethyl] cinnamic acid, (170) 4- [2- [2- (N-isopropyl-benzenesulfonyl Fluorenylamino) -5-trifluoromethylphenoxy] ethyl] benzoic acid, (171) 2-methoxy-4- [2- (N-isopropyl-benzenesulfonylamino-5- Trifluoromethylphenoxymethyl] benzoic acid, (172) 2-hydroxy-4- [2- (N-isopropyl-benzenesulfonamido-5-trifluoromethylphenoxymethyl] benzoic acid , (173) 2-hydroxy-4- [2- (N-isopropyl-benzenesulfonamido-5-methylphenoxymethyl] benzoic acid, (174) 2-hydroxy-4-〇 (Ν · Isopropyl-benzenesulfonamido-5-chlorophenoxymethyl] benzoic acid, (175) 4- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethyl Aniline methyl ] Benzoic acid, printed by (176) 4- [N-methyl- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylbenzene [Amino] aminomethyl] benzoic acid, (177) 4- [2- [N- (1,3-dihydroxyprop-2-yl) benzenesulfonamido] -5-trifluoromethylphenoxymethyl ] Benzoic acid, (178) 4- [2- [N- (1,3-Dimethoxy-2-yl) benzenesulfonamido] -5-trifluoromethylphenoxymethyl] benzoic acid, ( 179) 4- [2- (N-isopropyl-2-hexenylsulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, this paper size applies to China National Standard (CNS) Α4 Specification (210 X 297 mm) 20 39331 523506 Η3 (180) 4- [2- (N-isopropyl-cyclopentylsulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (181) 4- [2- (N-isopropyl · cyclohexylsulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (182) 4- [2- (N-isopropyl -Cyclohexylsulfonamido) -5-methylphenoxymethyl] benzoic acid, (183) 4- [2- (N-isopropyl-isopropylsulfonamido) -5-trifluoro Methylphenoxymethyl] benzoic acid, (184) 4- [2- (N-isopropyl-isopropylsulfonamido) -5-methylphenoxymethyl] benzene Formic acid, (185) 4- [2- (N-isopropyl-isopropylsulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (186) 4- [2- (N -Isopropyl-cyclopentylsulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (187) 4- [2- (N-isopropyl-cyclohexylsulfonamido) 5-trifluoromethylphenoxymethyl] cinnamic acid, (188) 4- [2- [N- (N, N-dimethylaminocarbonylmethyl) -benzenesulfonamido] -5-tri Fluoromethylphenoxymethyl] benzoic acid, (189) 4- (2-benzenesulfonamido-5-isopropylphenoxymethyl) benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau, Ministry of Economic Affairs, ( 190) 4- (2-benzenesulfonamido-5-ethylphenoxymethyl) benzoic acid, (191) 4- (2-benzenesulfonamido-5-hydroxymethylphenoxymethyl) benzene Formic acid, (192) 4- (2-benzenesulfonamidomethyl-5-chlorophenoxymethyl) benzoic acid, (193) 4- [2- (N-isopropyl-benzenesulfonamido) -5-Trifluoromethyl This paper is sized for the Chinese National Standard (CNS) A4 (210 X 297 mm) 21 39331 523506 H3 Phenoxymethyl] phenylpropionic acid printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs, (194 ) 4- (2-benzenesulfonamido-4-chlorophenoxymethyl) ) Benzyl alcohol, (195) 4- (2-benzylamido-5-chlorophenoxymethyl) benzoic acid, (196) 4- [2- (N-isopropyl-benzenesulfonamido) -5-isopropylphenoxymethyl] benzoic acid, (197) 4- [2- (N-methyl-benzenesulfonamido) -5-isopropylphenoxymethyl] benzoic acid, (198 ) 4- [2- (N-isopropyl-benzenesulfonamido) -5-ethylphenoxymethyl] benzoic acid, (199) 4- [2- (N-isopropyl-4-propyl Oxybenzenesulfonylamino) -5-trifluoromethylphenoxymethyl] benzoic acid, (200) 4- [2- (N-isopropyl-4-ethylthiobenzenesulfonylamino)- 5-trifluoromethylphenoxymethyl] benzoic acid, (201) 4- [2- (N-isopropyl-4-methylthiobenzenesulfonamido) -5-trifluoromethylphenoxymethyl Yl] benzoic acid, (202) 4- [2- (N-isopropyl-4-butoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (203) 4 -[2- (N-isopropyl-4-isopropoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid, (204) 4- [2- (N-iso Butyl-benzylamino) -5-chlorophenoxymethyl] benzoic acid, (205) 4- [2- (N-isopropyl-benzylamino) -5-trifluoromethylbenzene Oxymethyl] benzoic acid, (206) 6- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethyl Phenyloxymethyl] -2-naphthoic acid, (207) 4- [2- (N-isopropyl-butyrylamido) -5-trifluoromethylbenzene This paper is sized to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 22 39331 523506 _H3 oxymethyl] cinnamic acid, (208) 4- [2 · (N-isopropyl-4-ethoxybenzenesulfonamido) -5-trifluoro Methylphenoxymethyl] cinnamic acid, (209) 4- [2- (N-isobutyl-4-ethoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid or (210) 4- [2- (N-Isopropyl-3-ethoxybenzenesulfonamido) -5-trifluoromethylphenoxymethyl] benzoic acid or a methyl ester thereof. 11. For example, the sulfasalazine or urea derivative and its medically acceptable properties in the scope of patent application No. 1 are (1) 4- [2- | &gt; (4-chlorobenzenesulfonylamino) -5- Chlorophenyl]-(E) -vinyl] benzoic acid, (2) 4- [2- [2- (4-chlorobenzenesulfonamido) -5-chlorophenyl MZ) -vinyl] benzoic acid , (3) 4- [2- [2- (4-chlorophenyl) sulfonamido-5-chlorophenyl] ethyl] benzoic acid, (4) 4- [2- [2- (4- Chlorobenzenesulfonylamino) -5-chlorophenyl] ethynyl] benzoic acid, (5) 4- [2- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethyl Phenyl] ethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Bureau of Standards, Ministry of Economic Affairs (6) 4- [2- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethyl Phenylphenyl ME) -vinyl] benzoic acid or (7) 4- [2- [2- (N-isopropyl-benzenesulfonamido) -5-trifluoromethylphenyl]-(Z) -Vinyl] benzoic acid or its methyl ester. 12. For example, the sulfonamide or urea derivative and its pharmacologically acceptable properties in item 1 of the scope of patent application are (1) 4- [2- (N-isopropyl-2-thienylsulfonamido) -5-Chlorobenzene paper size applies Chinese National Standard (CNS) A4 specification (210 X 297 mm) 23 39331 523506 _ H3 oxymethyl] benzoic acid, (2) 4- [2- (N-isopropyl) -2-thienylsulfonamido) -5-methylphenoxymethyl] benzoic acid, (3) 4- [2- (N-isopropyl-2-furylsulfonamido) -5- Methylphenoxymethyl] benzoic acid, (4) 4- [2- (N-isopropyl-2-furylsulfonamido) -5-chlorophenoxymethyl] benzoic acid, (5) 4 -[2- (N-propyl-2-furylsulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (6) 4- [2- (N-propyl-2- Furylsulfonamido) -5-methylphenoxymethyl] benzoic acid, (7) 4- [2- [N- (isobutyl-2-furylsulfonamido) -5-methyl Phenoxymethyl] benzoic acid, (8) 4_ [2- [N- (isobutyl-2-furylsulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (9) 4- [2- [N- (prop-2-enyl) -2-furanylsulfonamido] -5-methylphenoxymethyl] benzoic acid, (10) 4- [2- [N- (2-methylpropan-2- ) -2-furanylsulfonamido] -5-methylphenoxymethyl] benzoic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (11) 4- [2- (N-isobutyl- 2-furanylsulfonamido) -4-methylphenoxymethyl] benzoic acid, (12) 4- [2- (N-isopropyl-2-furansulfonamido) -4-methyl Phenoxymethyl] benzoic acid, (13) 4- [2- [N- (2-methylprop-2-enyl) -2-furanylsulfonamido) -4-methylphenoxymethyl Benzyl] benzoic acid, (14) 4- [2-N-Isopropyl-2-furylsulfonamido-5-methylbenzene Paper size Applicable to Chinese National Standard (CNS) A4 (210 X 297) (%) 24 39331 523506 oxymethyl] cinnamic acid, (15) 4- [2-N-isopropyl-2-furylsulfonamido-5-trifluoromethylphenoxymethyl] cinnamic acid, ( 16) 4- [2-N-Isopropyl-2-furylsulfonamido-4-trifluoromethylphenoxymethyl] benzoic acid, (17) 4- [2-N-isobutyl- 2-furylsulfonamido-4-trifluoromethylphenoxymethyl] benzoic acid, (18) 4- [2-N-isobutyl-2-furylsulfonamido-5-chlorobenzene Oxymethyl] benzoic acid, (19) 4- [2-N-Isopropyl-2-furylsulfonamido-5-chlorophenoxymethyl] cinnamic acid, (20 ) 4- [2-N-isobutyl-2-furylsulfonamido-5-chlorophenoxymethyl] cinnamic acid, (21) 4- [2-N-isobutyl-2-furanyl Sulfonyl-5-trifluoromethylphenoxymethyl] benzoic acid, (22) 4- [2-N-Isobutyl-2-furylsulfonamido-4-chlorophenoxymethyl] Benzoic acid, (23) 4- [2-N-isobutyl-2-furylsulfonamido-4-methylphenoxymethyl] cinnamic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (24 ) 4- [2-N-isopropyl-2-furylsulfonamido-5-trifluoromethylphenoxymethyl] benzoic acid, (25) 4- [2-N-isopropyl-2 -Thienylsulfonamido-5-trifluoromethylphenoxymethyl] benzoic acid, (26) 4- [2- [N- (2-hydroxy-2-methylpropyl) -2-thienyl Sulfonamido] -5-trifluoromethylphenoxymethyl] benzoic acid, (27) 4- [2- (N-isopropyl-2-furanamido) -5-trifluoromethyl Standards apply to Chinese National Standard (CNS) A4 specifications (210 X 297 mm) 25 39331 523506 _H3 phenoxymethyl] benzoic acid, (28) 4- [2- (2-thienylsulfonamido) -5- Chlorobenzylamino] benzoic acid, (29) 4- [2- (N-isopropyl-2-furylsulfonamido) -5-methylphenylthiomethyl) Benzoic acid, (30) 4- [2- (N-isobutyl-2-thienylsulfonamido) -5-trifluoromethylphenoxymethyl] cinnamic acid, (31) 4- [2- (N-isopropyl-2-furanamidino) -5-trifluoromethylphenoxymethyl] cinnamic acid or (32) 4- [2- (N-isobutyl-2-furanamidino) ) -5-trifluoromethylphenoxymethyl] cinnamic acid or its methyl ester. Π. If the sulfonamide or urea derivative and its pharmaceutical acceptability in item 1 of the scope of the application for patent are (1) 5- [2- (N-isopropyl-benzenesulfonamido) -5- Methylphenoxymethyl] furan-2-carboxylic acid, (2) 6- (2-benzenesulfonamido-5-chlorophenoxymethyl) nicotinic acid, (3) 5- [2- (N -Isopropyl-benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] thiophene-2-carboxylic acid, printed by the Staff Welfare Committee of the Central Standards Bureau of the Ministry of Economic Affairs (4) 5- [2- (N -Isopropyl-benzenesulfonylamino) -5-trifluoromethylphenoxymethyl] furan-2-carboxylic acid, (5) 5- [2- (N-isopropyl-benzenesulfonylamino) ) -5-methylphenoxymethyl] thiophene-2-carboxylic acid, (6) 5- [2- (N-isopropyl-benzenesulfonamido) -5-chlorophenoxymethyl] thiophene- 2-carboxylic acid, (7) 5- [2- (N-isopropyl-benzenesulfonamido) -5-chlorophenoxymethyl] This paper size applies to China National Standard (CNS) A4 (210 X 297 mm) 26 39331 523506 __H3_ furan-2-unsaturated acid or (8) 4- (3-benzenesulfonamido-5-trifluoromethylpyridin-2-yloxymethyl) benzoic acid, or its formate ester. 14. The compound according to item 1 of the scope of patent application, wherein the compound is the compound (1) 4- [3- (N-isopropyl-5-methyl-2-furylsulfonamido) naphthalene Fluoren-2-yloxymethyl] cinnamic acid, (2) 4- [6- (N-methyl-5-methyl-2-furansulfonamido) indan-5-yloxymethyl Group] cinnamic acid or (3) 3-methyl-4- [2- (N-methyl- (4-methyl-2-thienylsulfonyl) amino) -4,5-dimethylbenzene Oxymethyl] benzoic acid or methyl esters of these compounds. 15. A pharmaceutical composition of a prostaglandin E2 antagonist or agonist, which contains a sulfonamide or a urea derivative of the general formula (1) as shown in item 1 of the scope of patent application, or a pharmaceutically acceptable 可接受 thereof as effective ingredient. Printed by the Staff Welfare Committee of the Central Bureau of Standards, Ministry of Economic Affairs This paper is sized to the Chinese National Standard (CNS) A4 (210 X 297 mm) 27 39331
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Families Citing this family (101)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19830431A1 (en) 1998-07-08 2000-01-13 Hoechst Marion Roussel De Gmbh Sulfonylamino-carboxylic acid N-arylamides as guanylate cyclase activators
HRP990246A2 (en) 1998-08-07 2000-06-30 Du Pont Pharm Co Succinoylamino benzodiazepines as inhibitors of a beta protein production
NZ525513A (en) 1998-08-07 2004-09-24 Pont Pharmaceuticals Du Succinoylamino lactams as inhibitors of Abeta protein production
GB9824579D0 (en) 1998-11-10 1999-01-06 Novartis Ag Organic compounds
BR9917082A (en) 1998-12-24 2001-11-06 Du Pont Pharm Co Compounds that inhibit the production of "beta" proteins, a method of treating neurological disorders associated with the production of "beta" -amyloid, pharmaceutical composition and, method of inhibiting y-secretase activity
HUP0200258A2 (en) 1999-03-05 2002-05-29 The Procter & Gamble Co. C16 unsaturated fp-selective prostaglandins analogs, pharmaceutical compositions containing them and their use
CZ20014642A3 (en) * 1999-06-24 2002-06-12 Smithkline Beecham Corporation Antagonist of macrophage catcher receptor
US6894175B1 (en) 1999-08-04 2005-05-17 The Procter & Gamble Company 2-Decarboxy-2-phosphinico prostaglandin derivatives and methods for their preparation and use
AU7052300A (en) * 1999-08-27 2001-03-26 Eli Lilly And Company Hypoglycemic n,n-arylsulfonylglycine compounds
US6960576B2 (en) 1999-09-13 2005-11-01 Bristol-Myers Squibb Pharma Company Hydroxyalkanoylaminolactams and related structures as inhibitors of Aβ protein production
US6503902B2 (en) 1999-09-13 2003-01-07 Bristol-Myers Squibb Pharma Company Hydroxyalkanoylaminolactams and related structures as inhibitors of a β protein production
AU7997700A (en) 1999-10-08 2001-04-23 Du Pont Pharmaceuticals Company Amino lactam sulfonamides as inhibitors of abeta protein production
EP1261610A2 (en) 2000-02-17 2002-12-04 Bristol-Myers Squibb Pharma Company Succinoylamino carbocycles and heterocycles as inhibitors of a-beta protein production
US6495540B2 (en) 2000-03-28 2002-12-17 Bristol - Myers Squibb Pharma Company Lactams as inhibitors of A-β protein production
US20020172693A1 (en) 2000-03-31 2002-11-21 Delong Michell Anthony Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
US20020013294A1 (en) 2000-03-31 2002-01-31 Delong Mitchell Anthony Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives
MXPA02009755A (en) 2000-04-03 2003-03-27 Bristol Myers Squibb Pharma Co CYCLIC LACTAMS AS INHIBITORS OF Abeta PROTEIN PRODUCTION.
BR0110051A (en) 2000-04-03 2004-12-07 Bristol Myers Squibb Pharma Co Compound, Compound Use, Pharmaceutical Composition and Method of Treatment of Alzheimer's Disease
AU2001257006A1 (en) 2000-04-11 2001-10-23 Du Pont Pharmaceuticals Company Substituted lactams as inhibitors of abeta protein production
AU783857B2 (en) 2000-06-01 2005-12-15 Bristol-Myers Squibb Pharma Company Lactams substituted by cyclic succinates as inhibitors of a beta protein production
GB2365426A (en) * 2000-08-01 2002-02-20 Pantherix Ltd Bactericidal benzamide derivatives
US7102009B2 (en) 2001-01-12 2006-09-05 Amgen Inc. Substituted amine derivatives and methods of use
US6995162B2 (en) 2001-01-12 2006-02-07 Amgen Inc. Substituted alkylamine derivatives and methods of use
US7105682B2 (en) 2001-01-12 2006-09-12 Amgen Inc. Substituted amine derivatives and methods of use
US20030134836A1 (en) * 2001-01-12 2003-07-17 Amgen Inc. Substituted arylamine derivatives and methods of use
US6878714B2 (en) 2001-01-12 2005-04-12 Amgen Inc. Substituted alkylamine derivatives and methods of use
DK1369419T3 (en) 2001-03-12 2007-09-24 Ono Pharmaceutical Co N-phenylarylsulfonamide compound, drug containing the compound as an active ingredient, intermediate of the compound and methods of preparation thereof
SE0100873D0 (en) * 2001-03-13 2001-03-13 Astrazeneca Ab Method of treatment
JP4175113B2 (en) 2001-03-14 2008-11-05 小野薬品工業株式会社 A therapeutic agent for depression containing an EP1 antagonist as an active ingredient
US6864255B2 (en) 2001-04-11 2005-03-08 Amgen Inc. Substituted triazinyl amide derivatives and methods of use
DE10121003A1 (en) 2001-04-28 2002-12-19 Aventis Pharma Gmbh Anthranilic acid amides, processes for their preparation, their use as medicaments and pharmaceutical preparations containing them
US20030216449A1 (en) * 2001-05-11 2003-11-20 Joseph Weinstock Phosphate transport inhibitors
GB0112834D0 (en) 2001-05-25 2001-07-18 Smithkline Beecham Plc Medicaments
US8329924B2 (en) * 2001-06-11 2012-12-11 Vertex Pharmaceuticals (Canada) Incorporated Compounds and methods for the treatment or prevention of Flavivirus infections
MXPA03011452A (en) * 2001-06-11 2005-03-07 Virochem Pharma Inc Thiophene derivatives as antiviral agents for flavivirus infection.
DE10128331A1 (en) 2001-06-12 2002-12-19 Aventis Pharma Gmbh New 2-(heteroarylsulfonyl-amino)-benzamide derivatives, which are potassium ion channel blocking antiarrhythmic agents, useful for e.g. treating atrial fibrillation or flutter
US20060100195A1 (en) * 2001-11-19 2006-05-11 Takayuki Maruyama Remedies for urinary frequency
KR101018318B1 (en) * 2001-12-21 2011-03-04 노보 노르디스크 에이/에스 Amide derivatives as gk activators
US7119120B2 (en) * 2001-12-26 2006-10-10 Genzyme Corporation Phosphate transport inhibitors
US7119112B2 (en) * 2002-02-28 2006-10-10 Icagen, Inc. Sulfonamides as potassium channel blockers
AU2003248549B2 (en) * 2002-05-24 2010-04-08 Millennium Pharmaceuticals, Inc. CCR9 inhibitors and methods of use thereof
AU2003243921B2 (en) * 2002-06-27 2009-05-07 Novo Nordisk A/S Aryl carbonyl derivatives as therapeutic agents
US7307088B2 (en) 2002-07-09 2007-12-11 Amgen Inc. Substituted anthranilic amide derivatives and methods of use
WO2004009581A1 (en) * 2002-07-24 2004-01-29 Mitsui Chemicals, Inc. Process for producing 2-alkyl-3-aminothiophene derivative
US6989399B2 (en) * 2002-08-01 2006-01-24 Bristol-Myers Squibb Company Antiamyloid phenylsulfonamides: N-alkanol derivatives
MXPA05003054A (en) 2002-09-20 2005-05-27 Pfizer Prod Inc Amide and sulfonamide ligands for the estrogen receptor.
KR20050043988A (en) * 2002-10-11 2005-05-11 액테리온 파마슈티칼 리미티드 Sulfonylamino-acetic acid derivatives and their use as orexin receptor antagonists
EP1798223B2 (en) 2002-11-18 2014-07-30 ChemoCentryx, Inc. Aryl sulfonamides
US7227035B2 (en) * 2002-11-18 2007-06-05 Chemocentryx Bis-aryl sulfonamides
US20070021466A1 (en) * 2002-11-18 2007-01-25 Solomon Ungashe CCR2 inhibitors and methods of use thereof
US7420055B2 (en) * 2002-11-18 2008-09-02 Chemocentryx, Inc. Aryl sulfonamides
US7741519B2 (en) 2007-04-23 2010-06-22 Chemocentryx, Inc. Bis-aryl sulfonamides
KR101058696B1 (en) 2002-12-10 2011-08-22 바이로켐 파마 인코포레이티드 Compounds and Methods for the Treatment or Prevention of Furabivirus Infections
MXPA05006701A (en) * 2002-12-20 2006-03-30 Amgen Inc Asthma and allergic inflammation modulators.
JP4681548B2 (en) 2003-07-22 2011-05-11 アステックス・セラピューティクス・リミテッド 3,4-disubstituted 1H-pyrazole compounds and their use as cyclin dependent kinase (CDK) and glycogen synthetase kinase-3 (GSK-3) modulators
EP1663979B1 (en) * 2003-09-03 2013-10-09 RaQualia Pharma Inc. Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists
EP1661889A4 (en) * 2003-09-05 2009-08-05 Ono Pharmaceutical Co Chemokine receptor antagonist and medical use thereof
BRPI0506662B8 (en) * 2004-01-06 2021-05-25 Novo Nordisk As glucokinase activating compounds
AU2005238291A1 (en) * 2004-05-04 2005-11-10 Pfizer Inc. Substituted methyl aryl or heteroaryl amide compounds
FR2872159B1 (en) * 2004-06-28 2007-10-05 Merck Sante Soc Par Actions Si NOVEL PHENYL CARBOXYLIC ACID DERIVATIVES AND THEIR USE IN THE TREATMENT OF DIABETES
US7906552B2 (en) 2004-08-10 2011-03-15 Allergan, Inc. Cyclopentane heptan(ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents
US7183310B2 (en) * 2004-08-10 2007-02-27 Allergan, Inc. Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
SE0402635D0 (en) * 2004-10-29 2004-10-29 Astrazeneca Ab Chemical compounds
US9040558B2 (en) 2004-12-31 2015-05-26 Dr. Reddy's Laboratories Ltd. Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors
US8604055B2 (en) 2004-12-31 2013-12-10 Dr. Reddy's Laboratories Ltd. Substituted benzylamino quinolines as cholesterol ester-transfer protein inhibitors
AR054425A1 (en) 2005-01-21 2007-06-27 Astex Therapeutics Ltd PIPERIDIN ADDITION SALTS 4-IL-ACID AMID 4- (2,6-DICLORO-BENZOILAMINO) 1H-PIRAZOL-3-CARBOXILICO.
US8404718B2 (en) 2005-01-21 2013-03-26 Astex Therapeutics Limited Combinations of pyrazole kinase inhibitors
JP2008189549A (en) * 2005-05-12 2008-08-21 Astellas Pharma Inc Carboxylic acid derivative or its salt
EA016071B1 (en) * 2005-05-13 2012-01-30 Вирокем Фарма Инк. Compounds and methods for the treatment or prevention of flavivirus infections
EP1904466A1 (en) * 2005-07-08 2008-04-02 Novo Nordisk A/S Dicycloalkyl urea glucokinase activators
US7999114B2 (en) * 2005-07-08 2011-08-16 Novo Nordisk A/S Dicycloalkylcarbamoyl ureas as glucokinase activators
JP4960355B2 (en) * 2005-07-14 2012-06-27 ノボ・ノルデイスク・エー／エス Urea-type glucokinase activator
US8247556B2 (en) * 2005-10-21 2012-08-21 Amgen Inc. Method for preparing 6-substituted-7-aza-indoles
JP2009057282A (en) * 2005-12-19 2009-03-19 Astellas Pharma Inc Carboxylic acid derivative or salt thereof
GB0526252D0 (en) * 2005-12-22 2006-02-01 Novartis Ag Organic compounds
TW200817319A (en) * 2006-08-10 2008-04-16 Astellas Pharma Inc Sulfonamide compound or salt thereof
AU2007321677B2 (en) 2006-11-15 2013-04-11 Vertex Pharmaceuticals (Canada) Incorporated Thiophene analogues for the treatment or prevention of flavivirus infections
TW200829578A (en) 2006-11-23 2008-07-16 Astrazeneca Ab Chemical compounds 537
JO2754B1 (en) 2006-12-21 2014-03-15 استرازينكا ايه بي Indazolyl amide derivatives for the treatment of glucocorticoid receptor mediated disorders
US8138185B2 (en) * 2007-01-09 2012-03-20 Novo Nordisk A/S Urea glucokinase activators
US8318778B2 (en) * 2007-01-11 2012-11-27 Novo Nordisk A/S Urea glucokinase activators
ES2437323T3 (en) 2007-02-16 2014-01-10 Ono Pharmaceutical Co., Ltd. Therapeutic agent for urination disorders
KR20100102668A (en) 2007-12-19 2010-09-24 암젠 인크 Phenyl acetic acid derivatives as inflammation modulators
HUE042839T2 (en) * 2008-03-12 2019-07-29 Ube Industries Pyridylaminoacetic acid compound
UY31831A (en) 2008-05-20 2010-01-05 Astrazeneca Ab DERIVATIVES OF INDAZOLS REPLACED WITH PHENYLL OR PIRIDINYL
MX2010014232A (en) 2008-06-23 2011-03-25 Astellas Pharma Inc Sulfonamide compound or salt thereof.
CA2757291C (en) 2009-03-30 2017-05-23 Ube Industries, Ltd. Medical composition for treatment or prophylaxis of glaucoma
MX2011013108A (en) * 2009-06-19 2012-01-20 Basf Se Herbicidal benzoxazinones.
CA2773997A1 (en) * 2009-09-11 2011-03-17 Ube Industries, Ltd. Aniline compound
WO2011030872A1 (en) * 2009-09-11 2011-03-17 宇部興産株式会社 Sulfonamide compounds
WO2011030873A1 (en) * 2009-09-11 2011-03-17 宇部興産株式会社 Benzyl compounds
WO2011030865A1 (en) * 2009-09-11 2011-03-17 宇部興産株式会社 Substituted zenzyl compounds
KR101967936B1 (en) * 2010-12-16 2019-04-10 알러간, 인코포레이티드 Sulfur derivatives as chemokine receptor modulators
CA2845284C (en) 2011-08-18 2018-03-06 Dr. Reddy's Laboratories Ltd. Substituted heterocyclic amine compounds as cholesteryl ester-transfer protein (cetp) inhibitors
CA2850022C (en) 2011-09-27 2018-05-01 Dr. Reddy's Laboratories, Ltd. 5 - benzylaminomethyl - 6 - aminopyrazolo [3,4-b] pyridine derivatives as cholesteryl ester-transfer protein (cetp) inhibitors useful for the treatment of atherosclerosis
CN105315180A (en) * 2014-06-05 2016-02-10 康志云 Novel sulfonylaniline compound and its preparation method and medical use
JP2021526130A (en) 2018-06-12 2021-09-30 ブイティーブイ・セラピューティクス・エルエルシー Therapeutic use of glucokinase activators in combination with insulin or insulin analogs
AU2019313082A1 (en) 2018-07-31 2021-02-18 Ono Pharmaceutical Co., Ltd. Benzene derivative
EP3898588B1 (en) 2018-12-21 2023-01-11 Merck Patent GmbH Disubstituted alkyne derivatives
US10836729B1 (en) * 2020-05-04 2020-11-17 King Abdulaziz University Metabolically stable 5-HMF derivatives for the treatment of hypoxia
WO2021249969A1 (en) 2020-06-10 2021-12-16 Merck Patent Gmbh Combination product for the treatment of cancer diseases

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3655693A (en) * 1969-06-25 1972-04-11 Merck & Co Inc Anti-inflammatory salicyclic acid derivatives
JPS5916871A (en) * 1982-07-20 1984-01-28 Shionogi & Co Ltd Sulfonamide-based benzamides
JPH0272150A (en) * 1988-09-06 1990-03-12 Otsuka Pharmaceut Factory Inc Sulfonamide derivative
CA2057324A1 (en) * 1990-12-18 1992-06-19 Lora Louise Fitch Benzamide and sulfonamide hypoglycemic agents
US5545669A (en) 1994-06-02 1996-08-13 Adams; Jerry L. Anti-inflammatory compounds
GB9514160D0 (en) 1994-07-25 1995-09-13 Zeneca Ltd Aromatic compounds
GB9417532D0 (en) 1994-08-31 1994-10-19 Zeneca Ltd Aromatic compounds
GB9420557D0 (en) 1994-10-12 1994-11-30 Zeneca Ltd Aromatic compounds

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